Comments on a novel synthesis of diethyl 1-aminoarylmethylphosphonates on the surface of alumina

Tetrahedron Letters

Volumn 44, Issue 9, 2003, Pages 1863-1865

  Soroka, Mirosław ^a   Kołodziejczyk, Krzysztof ^a  

^a WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Addition reaction; Aminoalkylation; Aminophosphonate; Hydrobenzamide; Imine

Indexed keywords

ALDEHYDE DERIVATIVE; ALKANE DERIVATIVE; ALUMINUM OXIDE; BENZAMIDE DERIVATIVE; HEXAMETHYLDISILAZANE; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; SOLID; SYNTHESIS;

EID: 0037463519     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00112-6     Document Type: Article

References (67)

1. Sardarian A.R., Kaboudin B. Tetrahedron Lett. 38:1997;2543-2546.
2. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
3. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
4. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
5. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
6. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
7. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
8. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
9. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
10. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
11. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
12. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
13. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
14. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
15. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
16. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
17. The 1-amino-1-arylmethylphosphonates are very well known compounds. For examples of their previous preparation, see: (a) Chalmers, M. E.; Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 5278; (b) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877; (c) Issleib, K.; Doepfer, K.-P.; Balszuweit, A. Z. Naturforsch. B Anorg. Chem. Org. Chem. 1981, 36, 1392; (d) Kabachnik, M. I.; Medwed', T. Ya. Izv. Akad. Nauk SSSR Ser. Khim. 1953, 868; Kabachnik, M. I.; Medwed', T. Ya. Dokl. AN SSSR 1952, 83, 689; (e) Kreutzkamp, N.; Cordes, G. Justus Liebigs Ann. Chem. 1959, 623, 103; (f) Krzyzanowska, B.; Stec, W. J. Synthesis 1978, 521; (g) Kudzin, Z. H.; Kotynski, A. Synthesis 1980, 1028; (h) Kudzin, Z. H.; Majchrzak, M. W. J. Organomet. Chem. 1989, 376, 245; (i) Lukszo, J.; Tyka, R. Pol. J. Chem. 1978, 52, 959; (j) Lukszo, J.; Tyka, R. Synthesis 1977, 239; (k) Rachon, J.; Wasielewski, C. Rocz. Chem. 1975, 49, 397; (l) Takahashi, H.; Yoshioka, M.; Imai, N.; Onimura, K.; Kobayashi, S. Synthesis 1994, 763; (m) Topolski, M.; Rachon, J. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 97; (n) Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528; (o) Yuan, C.; Wang, G.; Chen, S. Synthesis 1990, 522.
18. The N-arylidene-1-amino-1-arylmethylphosphonates were also described previously. See for examples: (a) Dehnel, A.; Kanabus-Kaminska, J. M.; Lavielle, G. Can. J. Chem. 1988, 66, 310; (b) Dehnel, A.; Finet, J. P.; Lavielle, G. Synthesis 1977, 474; (c) Heymes, A.; Chekroun, I. Synthesis 1987, 245; (d) Malenko, D. M.; Nesterova, L. I.; Luk'yanenko, S. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 1186; (e) Onis'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1996, 66, 1283; (f) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Prokopenko, V. P.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 523; (g) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1987, 57, 1233; (h) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1993, 63, 1906; (i) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1997, 67, 1642; (j) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Turov, A. V. Zh. Obshch. Khim. 1990, 60, 1425; (k) Russell, G. A.; Yao, C.-F. J. Org. Chem. 1992, 57, 6508; (l) Tupchienko, S. K.; Dudchenko, T. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1985, 55, 776.
19. The N-arylidene-1-amino-1-arylmethylphosphonates were also described previously. See for examples: (a) Dehnel, A.; Kanabus-Kaminska, J. M.; Lavielle, G. Can. J. Chem. 1988, 66, 310; (b) Dehnel, A.; Finet, J. P.; Lavielle, G. Synthesis 1977, 474; (c) Heymes, A.; Chekroun, I. Synthesis 1987, 245; (d) Malenko, D. M.; Nesterova, L. I.; Luk'yanenko, S. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 1186; (e) Onis'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1996, 66, 1283; (f) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Prokopenko, V. P.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 523; (g) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1987, 57, 1233; (h) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1993, 63, 1906; (i) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1997, 67, 1642; (j) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Turov, A. V. Zh. Obshch. Khim. 1990, 60, 1425; (k) Russell, G. A.; Yao, C.-F. J. Org. Chem. 1992, 57, 6508; (l) Tupchienko, S. K.; Dudchenko, T. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1985, 55, 776.
20. The N-arylidene-1-amino-1-arylmethylphosphonates were also described previously. See for examples: (a) Dehnel, A.; Kanabus-Kaminska, J. M.; Lavielle, G. Can. J. Chem. 1988, 66, 310; (b) Dehnel, A.; Finet, J. P.; Lavielle, G. Synthesis 1977, 474; (c) Heymes, A.; Chekroun, I. Synthesis 1987, 245; (d) Malenko, D. M.; Nesterova, L. I.; Luk'yanenko, S. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 1186; (e) Onis'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1996, 66, 1283; (f) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Prokopenko, V. P.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 523; (g) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1987, 57, 1233; (h) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1993, 63, 1906; (i) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1997, 67, 1642; (j) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Turov, A. V. Zh. Obshch. Khim. 1990, 60, 1425; (k) Russell, G. A.; Yao, C.-F. J. Org. Chem. 1992, 57, 6508; (l) Tupchienko, S. K.; Dudchenko, T. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1985, 55, 776.
21. The N-arylidene-1-amino-1-arylmethylphosphonates were also described previously. See for examples: (a) Dehnel, A.; Kanabus-Kaminska, J. M.; Lavielle, G. Can. J. Chem. 1988, 66, 310; (b) Dehnel, A.; Finet, J. P.; Lavielle, G. Synthesis 1977, 474; (c) Heymes, A.; Chekroun, I. Synthesis 1987, 245; (d) Malenko, D. M.; Nesterova, L. I.; Luk'yanenko, S. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 1186; (e) Onis'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1996, 66, 1283; (f) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Prokopenko, V. P.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 523; (g) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1987, 57, 1233; (h) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1993, 63, 1906; (i) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1997, 67, 1642; (j) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Turov, A. V. Zh. Obshch. Khim. 1990, 60, 1425; (k) Russell, G. A.; Yao, C.-F. J. Org. Chem. 1992, 57, 6508; (l) Tupchienko, S. K.; Dudchenko, T. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1985, 55, 776.
22. The N-arylidene-1-amino-1-arylmethylphosphonates were also described previously. See for examples: (a) Dehnel, A.; Kanabus-Kaminska, J. M.; Lavielle, G. Can. J. Chem. 1988, 66, 310; (b) Dehnel, A.; Finet, J. P.; Lavielle, G. Synthesis 1977, 474; (c) Heymes, A.; Chekroun, I. Synthesis 1987, 245; (d) Malenko, D. M.; Nesterova, L. I.; Luk'yanenko, S. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 1186; (e) Onis'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1996, 66, 1283; (f) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Prokopenko, V. P.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 523; (g) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1987, 57, 1233; (h) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1993, 63, 1906; (i) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1997, 67, 1642; (j) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Turov, A. V. Zh. Obshch. Khim. 1990, 60, 1425; (k) Russell, G. A.; Yao, C.-F. J. Org. Chem. 1992, 57, 6508; (l) Tupchienko, S. K.; Dudchenko, T. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1985, 55, 776.
23. The N-arylidene-1-amino-1-arylmethylphosphonates were also described previously. See for examples: (a) Dehnel, A.; Kanabus-Kaminska, J. M.; Lavielle, G. Can. J. Chem. 1988, 66, 310; (b) Dehnel, A.; Finet, J. P.; Lavielle, G. Synthesis 1977, 474; (c) Heymes, A.; Chekroun, I. Synthesis 1987, 245; (d) Malenko, D. M.; Nesterova, L. I.; Luk'yanenko, S. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 1186; (e) Onis'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1996, 66, 1283; (f) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Prokopenko, V. P.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 523; (g) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1987, 57, 1233; (h) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1993, 63, 1906; (i) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1997, 67, 1642; (j) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Turov, A. V. Zh. Obshch. Khim. 1990, 60, 1425; (k) Russell, G. A.; Yao, C.-F. J. Org. Chem. 1992, 57, 6508; (l) Tupchienko, S. K.; Dudchenko, T. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1985, 55, 776.
24. The N-arylidene-1-amino-1-arylmethylphosphonates were also described previously. See for examples: (a) Dehnel, A.; Kanabus-Kaminska, J. M.; Lavielle, G. Can. J. Chem. 1988, 66, 310; (b) Dehnel, A.; Finet, J. P.; Lavielle, G. Synthesis 1977, 474; (c) Heymes, A.; Chekroun, I. Synthesis 1987, 245; (d) Malenko, D. M.; Nesterova, L. I.; Luk'yanenko, S. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 1186; (e) Onis'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1996, 66, 1283; (f) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Prokopenko, V. P.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 523; (g) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1987, 57, 1233; (h) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1993, 63, 1906; (i) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1997, 67, 1642; (j) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Turov, A. V. Zh. Obshch. Khim. 1990, 60, 1425; (k) Russell, G. A.; Yao, C.-F. J. Org. Chem. 1992, 57, 6508; (l) Tupchienko, S. K.; Dudchenko, T. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1985, 55, 776.
25. The N-arylidene-1-amino-1-arylmethylphosphonates were also described previously. See for examples: (a) Dehnel, A.; Kanabus-Kaminska, J. M.; Lavielle, G. Can. J. Chem. 1988, 66, 310; (b) Dehnel, A.; Finet, J. P.; Lavielle, G. Synthesis 1977, 474; (c) Heymes, A.; Chekroun, I. Synthesis 1987, 245; (d) Malenko, D. M.; Nesterova, L. I.; Luk'yanenko, S. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 1186; (e) Onis'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1996, 66, 1283; (f) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Prokopenko, V. P.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 523; (g) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1987, 57, 1233; (h) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1993, 63, 1906; (i) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1997, 67, 1642; (j) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Turov, A. V. Zh. Obshch. Khim. 1990, 60, 1425; (k) Russell, G. A.; Yao, C.-F. J. Org. Chem. 1992, 57, 6508; (l) Tupchienko, S. K.; Dudchenko, T. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1985, 55, 776.
26. The N-arylidene-1-amino-1-arylmethylphosphonates were also described previously. See for examples: (a) Dehnel, A.; Kanabus-Kaminska, J. M.; Lavielle, G. Can. J. Chem. 1988, 66, 310; (b) Dehnel, A.; Finet, J. P.; Lavielle, G. Synthesis 1977, 474; (c) Heymes, A.; Chekroun, I. Synthesis 1987, 245; (d) Malenko, D. M.; Nesterova, L. I.; Luk'yanenko, S. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 1186; (e) Onis'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1996, 66, 1283; (f) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Prokopenko, V. P.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 523; (g) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1987, 57, 1233; (h) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1993, 63, 1906; (i) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1997, 67, 1642; (j) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Turov, A. V. Zh. Obshch. Khim. 1990, 60, 1425; (k) Russell, G. A.; Yao, C.-F. J. Org. Chem. 1992, 57, 6508; (l) Tupchienko, S. K.; Dudchenko, T. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1985, 55, 776.
27. The N-arylidene-1-amino-1-arylmethylphosphonates were also described previously. See for examples: (a) Dehnel, A.; Kanabus-Kaminska, J. M.; Lavielle, G. Can. J. Chem. 1988, 66, 310; (b) Dehnel, A.; Finet, J. P.; Lavielle, G. Synthesis 1977, 474; (c) Heymes, A.; Chekroun, I. Synthesis 1987, 245; (d) Malenko, D. M.; Nesterova, L. I.; Luk'yanenko, S. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 1186; (e) Onis'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1996, 66, 1283; (f) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Prokopenko, V. P.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 523; (g) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1987, 57, 1233; (h) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1993, 63, 1906; (i) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1997, 67, 1642; (j) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Turov, A. V. Zh. Obshch. Khim. 1990, 60, 1425; (k) Russell, G. A.; Yao, C.-F. J. Org. Chem. 1992, 57, 6508; (l) Tupchienko, S. K.; Dudchenko, T. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1985, 55, 776.
28. The N-arylidene-1-amino-1-arylmethylphosphonates were also described previously. See for examples: (a) Dehnel, A.; Kanabus-Kaminska, J. M.; Lavielle, G. Can. J. Chem. 1988, 66, 310; (b) Dehnel, A.; Finet, J. P.; Lavielle, G. Synthesis 1977, 474; (c) Heymes, A.; Chekroun, I. Synthesis 1987, 245; (d) Malenko, D. M.; Nesterova, L. I.; Luk'yanenko, S. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 1186; (e) Onis'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1996, 66, 1283; (f) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Prokopenko, V. P.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 523; (g) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1987, 57, 1233; (h) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1993, 63, 1906; (i) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1997, 67, 1642; (j) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Turov, A. V. Zh. Obshch. Khim. 1990, 60, 1425; (k) Russell, G. A.; Yao, C.-F. J. Org. Chem. 1992, 57, 6508; (l) Tupchienko, S. K.; Dudchenko, T. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1985, 55, 776.
29. The N-arylidene-1-amino-1-arylmethylphosphonates were also described previously. See for examples: (a) Dehnel, A.; Kanabus-Kaminska, J. M.; Lavielle, G. Can. J. Chem. 1988, 66, 310; (b) Dehnel, A.; Finet, J. P.; Lavielle, G. Synthesis 1977, 474; (c) Heymes, A.; Chekroun, I. Synthesis 1987, 245; (d) Malenko, D. M.; Nesterova, L. I.; Luk'yanenko, S. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 1186; (e) Onis'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1996, 66, 1283; (f) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Prokopenko, V. P.; Sinitsa, A. D. Zh. Obshch. Khim. 1990, 60, 523; (g) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1987, 57, 1233; (h) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1993, 63, 1906; (i) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D. Zh. Obshch. Khim. 1997, 67, 1642; (j) Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Turov, A. V. Zh. Obshch. Khim. 1990, 60, 1425; (k) Russell, G. A.; Yao, C.-F. J. Org. Chem. 1992, 57, 6508; (l) Tupchienko, S. K.; Dudchenko, T. N.; Sinitsa, A. D. Zh. Obshch. Khim. 1985, 55, 776.
30. Since the hexamethyldisilazane does not react with a freshly distilled dry aldehyde, a simple preparation of trimethylsilylimines in the reaction of an aldehyde with hexamethyldisilazane is possible only under harsh conditions for nonenolizable aldehydes. For a recent review see: (a) Panunzio, M.; Zarantonello, P. Org. Process Res. Develop. 1998, 2, 49-59. For examples of the preparation and use of N-trimethylsilylimines see: (b) Cainelli, G.; Giacomini, D.; Panunzio, M.; Martelli, G.; Spunta, G. Tetrahedron Lett. 1987, 28, 5369; (c) Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121; (d) Chan, L.-H.; Rochow, E. G. J. Organomet. Chem. 1967, 9, 231; (e) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vandervelde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676; (f) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366; (g) Guillemin, J.-C.; Ammi, L.; Denis, J.-M. Tetrahedron Lett. 1988, 29, 1287; (h) Ha, D.-C.; Hart, D. J.; Yang, T.-K. J. Am. Chem. Soc. 1984, 106, 4819; (i) Hart, D. J.; Kanai, K.-I.; Thomas, D. G.; Yang, T.-K. J. Org. Chem. 1983, 48, 289; (j) Kruger, C.; Rochow, E. G.; Wannagat, U. Chem. Ber. 1963, 96, 2132.
31. Since the hexamethyldisilazane does not react with a freshly distilled dry aldehyde, a simple preparation of trimethylsilylimines in the reaction of an aldehyde with hexamethyldisilazane is possible only under harsh conditions for nonenolizable aldehydes. For a recent review see: (a) Panunzio, M.; Zarantonello, P. Org. Process Res. Develop. 1998, 2, 49-59. For examples of the preparation and use of N-trimethylsilylimines see: (b) Cainelli, G.; Giacomini, D.; Panunzio, M.; Martelli, G.; Spunta, G. Tetrahedron Lett. 1987, 28, 5369; (c) Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121; (d) Chan, L.-H.; Rochow, E. G. J. Organomet. Chem. 1967, 9, 231; (e) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vandervelde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676; (f) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366; (g) Guillemin, J.-C.; Ammi, L.; Denis, J.-M. Tetrahedron Lett. 1988, 29, 1287; (h) Ha, D.-C.; Hart, D. J.; Yang, T.-K. J. Am. Chem. Soc. 1984, 106, 4819; (i) Hart, D. J.; Kanai, K.-I.; Thomas, D. G.; Yang, T.-K. J. Org. Chem. 1983, 48, 289; (j) Kruger, C.; Rochow, E. G.; Wannagat, U. Chem. Ber. 1963, 96, 2132.
32. Since the hexamethyldisilazane does not react with a freshly distilled dry aldehyde, a simple preparation of trimethylsilylimines in the reaction of an aldehyde with hexamethyldisilazane is possible only under harsh conditions for nonenolizable aldehydes. For a recent review see: (a) Panunzio, M.; Zarantonello, P. Org. Process Res. Develop. 1998, 2, 49-59. For examples of the preparation and use of N-trimethylsilylimines see: (b) Cainelli, G.; Giacomini, D.; Panunzio, M.; Martelli, G.; Spunta, G. Tetrahedron Lett. 1987, 28, 5369; (c) Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121; (d) Chan, L.-H.; Rochow, E. G. J. Organomet. Chem. 1967, 9, 231; (e) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vandervelde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676; (f) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366; (g) Guillemin, J.-C.; Ammi, L.; Denis, J.-M. Tetrahedron Lett. 1988, 29, 1287; (h) Ha, D.-C.; Hart, D. J.; Yang, T.-K. J. Am. Chem. Soc. 1984, 106, 4819; (i) Hart, D. J.; Kanai, K.-I.; Thomas, D. G.; Yang, T.-K. J. Org. Chem. 1983, 48, 289; (j) Kruger, C.; Rochow, E. G.; Wannagat, U. Chem. Ber. 1963, 96, 2132.
33. Since the hexamethyldisilazane does not react with a freshly distilled dry aldehyde, a simple preparation of trimethylsilylimines in the reaction of an aldehyde with hexamethyldisilazane is possible only under harsh conditions for nonenolizable aldehydes. For a recent review see: (a) Panunzio, M.; Zarantonello, P. Org. Process Res. Develop. 1998, 2, 49-59. For examples of the preparation and use of N-trimethylsilylimines see: (b) Cainelli, G.; Giacomini, D.; Panunzio, M.; Martelli, G.; Spunta, G. Tetrahedron Lett. 1987, 28, 5369; (c) Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121; (d) Chan, L.-H.; Rochow, E. G. J. Organomet. Chem. 1967, 9, 231; (e) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vandervelde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676; (f) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366; (g) Guillemin, J.-C.; Ammi, L.; Denis, J.-M. Tetrahedron Lett. 1988, 29, 1287; (h) Ha, D.-C.; Hart, D. J.; Yang, T.-K. J. Am. Chem. Soc. 1984, 106, 4819; (i) Hart, D. J.; Kanai, K.-I.; Thomas, D. G.; Yang, T.-K. J. Org. Chem. 1983, 48, 289; (j) Kruger, C.; Rochow, E. G.; Wannagat, U. Chem. Ber. 1963, 96, 2132.
34. Since the hexamethyldisilazane does not react with a freshly distilled dry aldehyde, a simple preparation of trimethylsilylimines in the reaction of an aldehyde with hexamethyldisilazane is possible only under harsh conditions for nonenolizable aldehydes. For a recent review see: (a) Panunzio, M.; Zarantonello, P. Org. Process Res. Develop. 1998, 2, 49-59. For examples of the preparation and use of N-trimethylsilylimines see: (b) Cainelli, G.; Giacomini, D.; Panunzio, M.; Martelli, G.; Spunta, G. Tetrahedron Lett. 1987, 28, 5369; (c) Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121; (d) Chan, L.-H.; Rochow, E. G. J. Organomet. Chem. 1967, 9, 231; (e) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vandervelde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676; (f) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366; (g) Guillemin, J.-C.; Ammi, L.; Denis, J.-M. Tetrahedron Lett. 1988, 29, 1287; (h) Ha, D.-C.; Hart, D. J.; Yang, T.-K. J. Am. Chem. Soc. 1984, 106, 4819; (i) Hart, D. J.; Kanai, K.-I.; Thomas, D. G.; Yang, T.-K. J. Org. Chem. 1983, 48, 289; (j) Kruger, C.; Rochow, E. G.; Wannagat, U. Chem. Ber. 1963, 96, 2132.
35. Since the hexamethyldisilazane does not react with a freshly distilled dry aldehyde, a simple preparation of trimethylsilylimines in the reaction of an aldehyde with hexamethyldisilazane is possible only under harsh conditions for nonenolizable aldehydes. For a recent review see: (a) Panunzio, M.; Zarantonello, P. Org. Process Res. Develop. 1998, 2, 49-59. For examples of the preparation and use of N-trimethylsilylimines see: (b) Cainelli, G.; Giacomini, D.; Panunzio, M.; Martelli, G.; Spunta, G. Tetrahedron Lett. 1987, 28, 5369; (c) Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121; (d) Chan, L.-H.; Rochow, E. G. J. Organomet. Chem. 1967, 9, 231; (e) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vandervelde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676; (f) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366; (g) Guillemin, J.-C.; Ammi, L.; Denis, J.-M. Tetrahedron Lett. 1988, 29, 1287; (h) Ha, D.-C.; Hart, D. J.; Yang, T.-K. J. Am. Chem. Soc. 1984, 106, 4819; (i) Hart, D. J.; Kanai, K.-I.; Thomas, D. G.; Yang, T.-K. J. Org. Chem. 1983, 48, 289; (j) Kruger, C.; Rochow, E. G.; Wannagat, U. Chem. Ber. 1963, 96, 2132.
36. Since the hexamethyldisilazane does not react with a freshly distilled dry aldehyde, a simple preparation of trimethylsilylimines in the reaction of an aldehyde with hexamethyldisilazane is possible only under harsh conditions for nonenolizable aldehydes. For a recent review see: (a) Panunzio, M.; Zarantonello, P. Org. Process Res. Develop. 1998, 2, 49-59. For examples of the preparation and use of N-trimethylsilylimines see: (b) Cainelli, G.; Giacomini, D.; Panunzio, M.; Martelli, G.; Spunta, G. Tetrahedron Lett. 1987, 28, 5369; (c) Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121; (d) Chan, L.-H.; Rochow, E. G. J. Organomet. Chem. 1967, 9, 231; (e) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vandervelde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676; (f) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366; (g) Guillemin, J.-C.; Ammi, L.; Denis, J.-M. Tetrahedron Lett. 1988, 29, 1287; (h) Ha, D.-C.; Hart, D. J.; Yang, T.-K. J. Am. Chem. Soc. 1984, 106, 4819; (i) Hart, D. J.; Kanai, K.-I.; Thomas, D. G.; Yang, T.-K. J. Org. Chem. 1983, 48, 289; (j) Kruger, C.; Rochow, E. G.; Wannagat, U. Chem. Ber. 1963, 96, 2132.
37. Since the hexamethyldisilazane does not react with a freshly distilled dry aldehyde, a simple preparation of trimethylsilylimines in the reaction of an aldehyde with hexamethyldisilazane is possible only under harsh conditions for nonenolizable aldehydes. For a recent review see: (a) Panunzio, M.; Zarantonello, P. Org. Process Res. Develop. 1998, 2, 49-59. For examples of the preparation and use of N-trimethylsilylimines see: (b) Cainelli, G.; Giacomini, D.; Panunzio, M.; Martelli, G.; Spunta, G. Tetrahedron Lett. 1987, 28, 5369; (c) Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121; (d) Chan, L.-H.; Rochow, E. G. J. Organomet. Chem. 1967, 9, 231; (e) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vandervelde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676; (f) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366; (g) Guillemin, J.-C.; Ammi, L.; Denis, J.-M. Tetrahedron Lett. 1988, 29, 1287; (h) Ha, D.-C.; Hart, D. J.; Yang, T.-K. J. Am. Chem. Soc. 1984, 106, 4819; (i) Hart, D. J.; Kanai, K.-I.; Thomas, D. G.; Yang, T.-K. J. Org. Chem. 1983, 48, 289; (j) Kruger, C.; Rochow, E. G.; Wannagat, U. Chem. Ber. 1963, 96, 2132.
38. Since the hexamethyldisilazane does not react with a freshly distilled dry aldehyde, a simple preparation of trimethylsilylimines in the reaction of an aldehyde with hexamethyldisilazane is possible only under harsh conditions for nonenolizable aldehydes. For a recent review see: (a) Panunzio, M.; Zarantonello, P. Org. Process Res. Develop. 1998, 2, 49-59. For examples of the preparation and use of N-trimethylsilylimines see: (b) Cainelli, G.; Giacomini, D.; Panunzio, M.; Martelli, G.; Spunta, G. Tetrahedron Lett. 1987, 28, 5369; (c) Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121; (d) Chan, L.-H.; Rochow, E. G. J. Organomet. Chem. 1967, 9, 231; (e) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vandervelde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676; (f) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366; (g) Guillemin, J.-C.; Ammi, L.; Denis, J.-M. Tetrahedron Lett. 1988, 29, 1287; (h) Ha, D.-C.; Hart, D. J.; Yang, T.-K. J. Am. Chem. Soc. 1984, 106, 4819; (i) Hart, D. J.; Kanai, K.-I.; Thomas, D. G.; Yang, T.-K. J. Org. Chem. 1983, 48, 289; (j) Kruger, C.; Rochow, E. G.; Wannagat, U. Chem. Ber. 1963, 96, 2132.
39. Since the hexamethyldisilazane does not react with a freshly distilled dry aldehyde, a simple preparation of trimethylsilylimines in the reaction of an aldehyde with hexamethyldisilazane is possible only under harsh conditions for nonenolizable aldehydes. For a recent review see: (a) Panunzio, M.; Zarantonello, P. Org. Process Res. Develop. 1998, 2, 49-59. For examples of the preparation and use of N-trimethylsilylimines see: (b) Cainelli, G.; Giacomini, D.; Panunzio, M.; Martelli, G.; Spunta, G. Tetrahedron Lett. 1987, 28, 5369; (c) Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121; (d) Chan, L.-H.; Rochow, E. G. J. Organomet. Chem. 1967, 9, 231; (e) Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Vandervelde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664-2676; (f) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366; (g) Guillemin, J.-C.; Ammi, L.; Denis, J.-M. Tetrahedron Lett. 1988, 29, 1287; (h) Ha, D.-C.; Hart, D. J.; Yang, T.-K. J. Am. Chem. Soc. 1984, 106, 4819; (i) Hart, D. J.; Kanai, K.-I.; Thomas, D. G.; Yang, T.-K. J. Org. Chem. 1983, 48, 289; (j) Kruger, C.; Rochow, E. G.; Wannagat, U. Chem. Ber. 1963, 96, 2132.
40. 2d in a reaction of ammonia, diethyl phosphite and an aldehyde (or ketones), the so called Kabachnik-Medved reaction - for a recent review see: (a) Cherkasov, R. A.; Galkin, V. I. Uspekhi Khim. 1998, 67, 940-968. However, the use of ammonia in this, Mannich type, reaction gave a rather low yield of the desired product. Imines are not the primary products of the reactions of ammonia with aldehydes or ketones. Ammonia reacts with formaldehyde to give hexamethylenetetramine, with aliphatic aldehydes to give 2,4,6-trialkyl-1,3,5-hexahydrotriazines and with aromatic aldehydes to give hydrobenzamides. For a disscussion see: (b) Nielsen, A. T.; Atkins, R. L.; Moore, D. W.; Scott, R.; Mallory, D.; LaBerge, J. M. J. Org. Chem. 1973, 38, 3288. Moreover, an equilibrium between hexahydrotriazines and imines has never been proved. Since the hexahydrotriazines react with diethyl phosphites to give complex mixtures of products with low yields of aminophosphonates, several groups have tried to improve the yield of aminoalkylation of tervalent phosphorus compound, essentially by introducing ammonia equivalents such as benzylamine: (c) Tyka R. Tetrahedron Lett. 1970, 9, 677; 1-phenylcyclopentylamine (see Refs 2i, j); benzhydrylamine (see Ref. 2c); and tritylamine: (d) Soroka, M.; Zygmunt, J. Synthesis 1988, 370. We have also tried hexamethyldisilazane as an ammonia equivalent. However, in the reaction of dry acetaldehyde with hexamethyldisilazane and diethyl phosphite we isolated only diethyl 1-trimethylsilyloxyethylphosphonate in almost quantitative yield without any trace of aminophosphonate. Similar results were obtained with benzaldehyde - also the trimethylsilylated 1-hydroxyphosphonate was the sole product of this reaction. In the cases of acetone or cyclohexanone the corresponding diethyl 1-hydroxyalkylphosphonates were isolated in crystalline states. According to our observation hexamethyldisilazane is an excellent base in the Abramov reaction: (d) Abramov, V. S. Zh. Obshch. Khim. 1952, 22, 647; and when 1-hydroxyalkylphosphonates are not sterically hindered, it is also a silylating agent which converts hydroxyphosphonic acids into their O-trimethylsilyl derivatives. O-trimethylsilyl-1-hydroxyalkylphosphonates are well known compounds. For examples see: (e) Nesterov, L. V.; Krepysheva, N. J.; Sabirova, R. A.; Romanova, G. N. Zh. Obshch. Khim. 1971, 41, 2449; (f) Novikova, Z. S.; Mashoshina, S. N.; Sapozhnikova, T. A.; Lutsenko, I. F. Zh. Obshch. Khim. 1970, 41, 2622; (g) Evans, D. A.; Hurst, K. M.; Takacs, J. M. J. Am. Chem. Soc. 1978, 100, 3467 and references cited therein.
41. 2d in a reaction of ammonia, diethyl phosphite and an aldehyde (or ketones), the so called Kabachnik-Medved reaction - for a recent review see: (a) Cherkasov, R. A.; Galkin, V. I. Uspekhi Khim. 1998, 67, 940-968. However, the use of ammonia in this, Mannich type, reaction gave a rather low yield of the desired product. Imines are not the primary products of the reactions of ammonia with aldehydes or ketones. Ammonia reacts with formaldehyde to give hexamethylenetetramine, with aliphatic aldehydes to give 2,4,6-trialkyl-1,3,5-hexahydrotriazines and with aromatic aldehydes to give hydrobenzamides. For a disscussion see: (b) Nielsen, A. T.; Atkins, R. L.; Moore, D. W.; Scott, R.; Mallory, D.; LaBerge, J. M. J. Org. Chem. 1973, 38, 3288. Moreover, an equilibrium between hexahydrotriazines and imines has never been proved. Since the hexahydrotriazines react with diethyl phosphites to give complex mixtures of products with low yields of aminophosphonates, several groups have tried to improve the yield of aminoalkylation of tervalent phosphorus compound, essentially by introducing ammonia equivalents such as benzylamine: (c) Tyka R. Tetrahedron Lett. 1970, 9, 677; 1-phenylcyclopentylamine (see Refs 2i, j); benzhydrylamine (see Ref. 2c); and tritylamine: (d) Soroka, M.; Zygmunt, J. Synthesis 1988, 370. We have also tried hexamethyldisilazane as an ammonia equivalent. However, in the reaction of dry acetaldehyde with hexamethyldisilazane and diethyl phosphite we isolated only diethyl 1-trimethylsilyloxyethylphosphonate in almost quantitative yield without any trace of aminophosphonate. Similar results were obtained with benzaldehyde - also the trimethylsilylated 1-hydroxyphosphonate was the sole product of this reaction. In the cases of acetone or cyclohexanone the corresponding diethyl 1-hydroxyalkylphosphonates were isolated in crystalline states. According to our observation hexamethyldisilazane is an excellent base in the Abramov reaction: (d) Abramov, V. S. Zh. Obshch. Khim. 1952, 22, 647; and when 1-hydroxyalkylphosphonates are not sterically hindered, it is also a silylating agent which converts hydroxyphosphonic acids into their O-trimethylsilyl derivatives. O-trimethylsilyl-1-hydroxyalkylphosphonates are well known compounds. For examples see: (e) Nesterov, L. V.; Krepysheva, N. J.; Sabirova, R. A.; Romanova, G. N. Zh. Obshch. Khim. 1971, 41, 2449; (f) Novikova, Z. S.; Mashoshina, S. N.; Sapozhnikova, T. A.; Lutsenko, I. F. Zh. Obshch. Khim. 1970, 41, 2622; (g) Evans, D. A.; Hurst, K. M.; Takacs, J. M. J. Am. Chem. Soc. 1978, 100, 3467 and references cited therein.
42. 2d in a reaction of ammonia, diethyl phosphite and an aldehyde (or ketones), the so called Kabachnik-Medved reaction - for a recent review see: (a) Cherkasov, R. A.; Galkin, V. I. Uspekhi Khim. 1998, 67, 940-968. However, the use of ammonia in this, Mannich type, reaction gave a rather low yield of the desired product. Imines are not the primary products of the reactions of ammonia with aldehydes or ketones. Ammonia reacts with formaldehyde to give hexamethylenetetramine, with aliphatic aldehydes to give 2,4,6-trialkyl-1,3,5-hexahydrotriazines and with aromatic aldehydes to give hydrobenzamides. For a disscussion see: (b) Nielsen, A. T.; Atkins, R. L.; Moore, D. W.; Scott, R.; Mallory, D.; LaBerge, J. M. J. Org. Chem. 1973, 38, 3288. Moreover, an equilibrium between hexahydrotriazines and imines has never been proved. Since the hexahydrotriazines react with diethyl phosphites to give complex mixtures of products with low yields of aminophosphonates, several groups have tried to improve the yield of aminoalkylation of tervalent phosphorus compound, essentially by introducing ammonia equivalents such as benzylamine: (c) Tyka R. Tetrahedron Lett. 1970, 9, 677; 1-phenylcyclopentylamine (see Refs 2i, j); benzhydrylamine (see Ref. 2c); and tritylamine: (d) Soroka, M.; Zygmunt, J. Synthesis 1988, 370. We have also tried hexamethyldisilazane as an ammonia equivalent. However, in the reaction of dry acetaldehyde with hexamethyldisilazane and diethyl phosphite we isolated only diethyl 1-trimethylsilyloxyethylphosphonate in almost quantitative yield without any trace of aminophosphonate. Similar results were obtained with benzaldehyde - also the trimethylsilylated 1-hydroxyphosphonate was the sole product of this reaction. In the cases of acetone or cyclohexanone the corresponding diethyl 1-hydroxyalkylphosphonates were isolated in crystalline states. According to our observation hexamethyldisilazane is an excellent base in the Abramov reaction: (d) Abramov, V. S. Zh. Obshch. Khim. 1952, 22, 647; and when 1-hydroxyalkylphosphonates are not sterically hindered, it is also a silylating agent which converts hydroxyphosphonic acids into their O-trimethylsilyl derivatives. O-trimethylsilyl-1-hydroxyalkylphosphonates are well known compounds. For examples see: (e) Nesterov, L. V.; Krepysheva, N. J.; Sabirova, R. A.; Romanova, G. N. Zh. Obshch. Khim. 1971, 41, 2449; (f) Novikova, Z. S.; Mashoshina, S. N.; Sapozhnikova, T. A.; Lutsenko, I. F. Zh. Obshch. Khim. 1970, 41, 2622; (g) Evans, D. A.; Hurst, K. M.; Takacs, J. M. J. Am. Chem. Soc. 1978, 100, 3467 and references cited therein.
43. 2d in a reaction of ammonia, diethyl phosphite and an aldehyde (or ketones), the so called Kabachnik-Medved reaction - for a recent review see: (a) Cherkasov, R. A.; Galkin, V. I. Uspekhi Khim. 1998, 67, 940-968. However, the use of ammonia in this, Mannich type, reaction gave a rather low yield of the desired product. Imines are not the primary products of the reactions of ammonia with aldehydes or ketones. Ammonia reacts with formaldehyde to give hexamethylenetetramine, with aliphatic aldehydes to give 2,4,6-trialkyl-1,3,5-hexahydrotriazines and with aromatic aldehydes to give hydrobenzamides. For a disscussion see: (b) Nielsen, A. T.; Atkins, R. L.; Moore, D. W.; Scott, R.; Mallory, D.; LaBerge, J. M. J. Org. Chem. 1973, 38, 3288. Moreover, an equilibrium between hexahydrotriazines and imines has never been proved. Since the hexahydrotriazines react with diethyl phosphites to give complex mixtures of products with low yields of aminophosphonates, several groups have tried to improve the yield of aminoalkylation of tervalent phosphorus compound, essentially by introducing ammonia equivalents such as benzylamine: (c) Tyka R. Tetrahedron Lett. 1970, 9, 677; 1-phenylcyclopentylamine (see Refs 2i, j); benzhydrylamine (see Ref. 2c); and tritylamine: (d) Soroka, M.; Zygmunt, J. Synthesis 1988, 370. We have also tried hexamethyldisilazane as an ammonia equivalent. However, in the reaction of dry acetaldehyde with hexamethyldisilazane and diethyl phosphite we isolated only diethyl 1-trimethylsilyloxyethylphosphonate in almost quantitative yield without any trace of aminophosphonate. Similar results were obtained with benzaldehyde - also the trimethylsilylated 1-hydroxyphosphonate was the sole product of this reaction. In the cases of acetone or cyclohexanone the corresponding diethyl 1-hydroxyalkylphosphonates were isolated in crystalline states. According to our observation hexamethyldisilazane is an excellent base in the Abramov reaction: (d) Abramov, V. S. Zh. Obshch. Khim. 1952, 22, 647; and when 1-hydroxyalkylphosphonates are not sterically hindered, it is also a silylating agent which converts hydroxyphosphonic acids into their O-trimethylsilyl derivatives. O-trimethylsilyl-1-hydroxyalkylphosphonates are well known compounds. For examples see: (e) Nesterov, L. V.; Krepysheva, N. J.; Sabirova, R. A.; Romanova, G. N. Zh. Obshch. Khim. 1971, 41, 2449; (f) Novikova, Z. S.; Mashoshina, S. N.; Sapozhnikova, T. A.; Lutsenko, I. F. Zh. Obshch. Khim. 1970, 41, 2622; (g) Evans, D. A.; Hurst, K. M.; Takacs, J. M. J. Am. Chem. Soc. 1978, 100, 3467 and references cited therein.
44. 2d in a reaction of ammonia, diethyl phosphite and an aldehyde (or ketones), the so called Kabachnik-Medved reaction - for a recent review see: (a) Cherkasov, R. A.; Galkin, V. I. Uspekhi Khim. 1998, 67, 940-968. However, the use of ammonia in this, Mannich type, reaction gave a rather low yield of the desired product. Imines are not the primary products of the reactions of ammonia with aldehydes or ketones. Ammonia reacts with formaldehyde to give hexamethylenetetramine, with aliphatic aldehydes to give 2,4,6-trialkyl-1,3,5-hexahydrotriazines and with aromatic aldehydes to give hydrobenzamides. For a disscussion see: (b) Nielsen, A. T.; Atkins, R. L.; Moore, D. W.; Scott, R.; Mallory, D.; LaBerge, J. M. J. Org. Chem. 1973, 38, 3288. Moreover, an equilibrium between hexahydrotriazines and imines has never been proved. Since the hexahydrotriazines react with diethyl phosphites to give complex mixtures of products with low yields of aminophosphonates, several groups have tried to improve the yield of aminoalkylation of tervalent phosphorus compound, essentially by introducing ammonia equivalents such as benzylamine: (c) Tyka R. Tetrahedron Lett. 1970, 9, 677; 1-phenylcyclopentylamine (see Refs 2i, j); benzhydrylamine (see Ref. 2c); and tritylamine: (d) Soroka, M.; Zygmunt, J. Synthesis 1988, 370. We have also tried hexamethyldisilazane as an ammonia equivalent. However, in the reaction of dry acetaldehyde with hexamethyldisilazane and diethyl phosphite we isolated only diethyl 1-trimethylsilyloxyethylphosphonate in almost quantitative yield without any trace of aminophosphonate. Similar results were obtained with benzaldehyde - also the trimethylsilylated 1-hydroxyphosphonate was the sole product of this reaction. In the cases of acetone or cyclohexanone the corresponding diethyl 1-hydroxyalkylphosphonates were isolated in crystalline states. According to our observation hexamethyldisilazane is an excellent base in the Abramov reaction: (d) Abramov, V. S. Zh. Obshch. Khim. 1952, 22, 647; and when 1-hydroxyalkylphosphonates are not sterically hindered, it is also a silylating agent which converts hydroxyphosphonic acids into their O-trimethylsilyl derivatives. O-trimethylsilyl-1-hydroxyalkylphosphonates are well known compounds. For examples see: (e) Nesterov, L. V.; Krepysheva, N. J.; Sabirova, R. A.; Romanova, G. N. Zh. Obshch. Khim. 1971, 41, 2449; (f) Novikova, Z. S.; Mashoshina, S. N.; Sapozhnikova, T. A.; Lutsenko, I. F. Zh. Obshch. Khim. 1970, 41, 2622; (g) Evans, D. A.; Hurst, K. M.; Takacs, J. M. J. Am. Chem. Soc. 1978, 100, 3467 and references cited therein.
45. 2d in a reaction of ammonia, diethyl phosphite and an aldehyde (or ketones), the so called Kabachnik-Medved reaction - for a recent review see: (a) Cherkasov, R. A.; Galkin, V. I. Uspekhi Khim. 1998, 67, 940-968. However, the use of ammonia in this, Mannich type, reaction gave a rather low yield of the desired product. Imines are not the primary products of the reactions of ammonia with aldehydes or ketones. Ammonia reacts with formaldehyde to give hexamethylenetetramine, with aliphatic aldehydes to give 2,4,6-trialkyl-1,3,5-hexahydrotriazines and with aromatic aldehydes to give hydrobenzamides. For a disscussion see: (b) Nielsen, A. T.; Atkins, R. L.; Moore, D. W.; Scott, R.; Mallory, D.; LaBerge, J. M. J. Org. Chem. 1973, 38, 3288. Moreover, an equilibrium between hexahydrotriazines and imines has never been proved. Since the hexahydrotriazines react with diethyl phosphites to give complex mixtures of products with low yields of aminophosphonates, several groups have tried to improve the yield of aminoalkylation of tervalent phosphorus compound, essentially by introducing ammonia equivalents such as benzylamine: (c) Tyka R. Tetrahedron Lett. 1970, 9, 677; 1-phenylcyclopentylamine (see Refs 2i, j); benzhydrylamine (see Ref. 2c); and tritylamine: (d) Soroka, M.; Zygmunt, J. Synthesis 1988, 370. We have also tried hexamethyldisilazane as an ammonia equivalent. However, in the reaction of dry acetaldehyde with hexamethyldisilazane and diethyl phosphite we isolated only diethyl 1-trimethylsilyloxyethylphosphonate in almost quantitative yield without any trace of aminophosphonate. Similar results were obtained with benzaldehyde - also the trimethylsilylated
46. 2d in a reaction of ammonia, diethyl phosphite and an aldehyde (or ketones), the so called Kabachnik-Medved reaction - for a recent review see: (a) Cherkasov, R. A.; Galkin, V. I. Uspekhi Khim. 1998, 67, 940-968. However, the use of ammonia in this, Mannich type, reaction gave a rather low yield of the desired product. Imines are not the primary products of the reactions of ammonia with aldehydes or ketones. Ammonia reacts with formaldehyde to give hexamethylenetetramine, with aliphatic aldehydes to give 2,4,6-trialkyl-1,3,5-hexahydrotriazines and with aromatic aldehydes to give hydrobenzamides. For a disscussion see: (b) Nielsen, A. T.; Atkins, R. L.; Moore, D. W.; Scott, R.; Mallory, D.; LaBerge, J. M. J. Org. Chem. 1973, 38, 3288. Moreover, an equilibrium between hexahydrotriazines and imines has never been proved. Since the hexahydrotriazines react with diethyl phosphites to give complex mixtures of products with low yields of aminophosphonates, several groups have tried to improve the yield of aminoalkylation of tervalent phosphorus compound, essentially by introducing ammonia equivalents such as benzylamine: (c) Tyka R. Tetrahedron Lett. 1970, 9, 677; 1-phenylcyclopentylamine (see Refs 2i, j); benzhydrylamine (see Ref. 2c); and tritylamine: (d) Soroka, M.; Zygmunt, J. Synthesis 1988, 370. We have also tried hexamethyldisilazane as an ammonia equivalent. However, in the reaction of dry acetaldehyde with hexamethyldisilazane and diethyl phosphite we isolated only diethyl 1-trimethylsilyloxyethylphosphonate in almost quantitative yield without any trace of aminophosphonate. Similar results were obtained with benzaldehyde - also the trimethylsilylated 1-hydroxyphosphonate was the sole product of this reaction. In the cases of acetone or cyclohexanone the corresponding diethyl 1-hydroxyalkylphosphonates were isolated in crystalline states. According to our observation hexamethyldisilazane is an excellent base in the Abramov reaction: (d) Abramov, V. S. Zh. Obshch. Khim. 1952, 22, 647; and when 1-hydroxyalkylphosphonates are not sterically hindered, it is also a silylating agent which converts hydroxyphosphonic acids into their O-trimethylsilyl derivatives. O-trimethylsilyl-1-hydroxyalkylphosphonates are well known compounds. For examples see: (e) Nesterov, L. V.; Krepysheva, N. J.; Sabirova, R. A.; Romanova, G. N. Zh. Obshch. Khim. 1971, 41, 2449; (f) Novikova, Z. S.; Mashoshina, S. N.; Sapozhnikova, T. A.; Lutsenko, I. F. Zh. Obshch. Khim. 1970, 41, 2622; (g) Evans, D. A.; Hurst, K. M.; Takacs, J. M. J. Am. Chem. Soc. 1978, 100, 3467 and references cited therein.
47. 2d in a reaction of ammonia, diethyl phosphite and an aldehyde (or ketones), the so called Kabachnik-Medved reaction - for a recent review see: (a) Cherkasov, R. A.; Galkin, V. I. Uspekhi Khim. 1998, 67, 940-968. However, the use of ammonia in this, Mannich type, reaction gave a rather low yield of the desired product. Imines are not the primary products of the reactions of ammonia with aldehydes or ketones. Ammonia reacts with formaldehyde to give hexamethylenetetramine, with aliphatic aldehydes to give 2,4,6-trialkyl-1,3,5-hexahydrotriazines and with aromatic aldehydes to give hydrobenzamides. For a disscussion see: (b) Nielsen, A. T.; Atkins, R. L.; Moore, D. W.; Scott, R.; Mallory, D.; LaBerge, J. M. J. Org. Chem. 1973, 38, 3288. Moreover, an equilibrium between hexahydrotriazines and imines has never been proved. Since the hexahydrotriazines react with diethyl phosphites to give complex mixtures of products with low yields of aminophosphonates, several groups have tried to improve the yield of aminoalkylation of tervalent phosphorus compound, essentially by introducing ammonia equivalents such as benzylamine: (c) Tyka R. Tetrahedron Lett. 1970, 9, 677; 1-phenylcyclopentylamine (see Refs 2i, j); benzhydrylamine (see Ref. 2c); and tritylamine: (d) Soroka, M.; Zygmunt, J. Synthesis 1988, 370. We have also tried hexamethyldisilazane as an ammonia equivalent. However, in the reaction of dry acetaldehyde with hexamethyldisilazane and diethyl phosphite we isolated only diethyl 1-trimethylsilyloxyethylphosphonate in almost quantitative yield without any trace of aminophosphonate. Similar results were obtained with benzaldehyde - also the trimethylsilylated 1-hydroxyphosphonate was the sole product of this reaction. In the cases of acetone or cyclohexanone the corresponding diethyl 1-hydroxyalkylphosphonates were isolated in crystalline states. According to our observation hexamethyldisilazane is an excellent base in the Abramov reaction: (d) Abramov, V. S. Zh. Obshch. Khim. 1952, 22, 647; and when 1-hydroxyalkylphosphonates are not sterically hindered, it is also a silylating agent which converts hydroxyphosphonic acids into their O-trimethylsilyl derivatives. O-trimethylsilyl-1-hydroxyalkylphosphonates are well known compounds. For examples see: (e) Nesterov, L. V.; Krepysheva, N. J.; Sabirova, R. A.; Romanova, G. N. Zh. Obshch. Khim. 1971, 41, 2449; (f) Novikova, Z. S.; Mashoshina, S. N.; Sapozhnikova, T. A.; Lutsenko, I. F. Zh. Obshch. Khim. 1970, 41, 2622; (g) Evans, D. A.; Hurst, K. M.; Takacs, J. M. J. Am. Chem. Soc. 1978, 100, 3467 and references cited therein.
48. When we mixed hexamethyldisilazane with any of the alumina samples we had in our stock, we have always observed ammonia evolution (by smell and by pH indicator paper). Mixing alumina with benzaldehyde and hexamethyldisilazane gave hydrobenzamide as the sole product after extraction and evaporation of the solvent. Addition of a few drops of a saturated ethereal solution of water into the mixture of acetaldehyde and hexamethyldisilazane in ether, resulted in precipitation of white crystals identified as 2,4,6-trimethyl-1,3,5-hexahydrotriazine-'acetaldehyde-ammonia trimer' (see Aldrich Catalogue, nr. 10.820-0). The same procedure in the case of benzaldehyde resulted in practically quantitative isolation of hydrobenzamide.
49. Hexamethyldisilazane is a very well known mild 'silanizing' agent. See Fluka's Silylating Agents; Fluka Chemie AG 1995 (ISBN 3-905617-13-7), p. 21 and 120.
50. Hydrobenzamide was described for the first time in 1836 by Laurent in the reaction of benzaldehyde ('Bittermandel öl') with gaseous ammonia: (a) Laurent, M. A. Ann. Pharm. 1837, 21, 130-134; 'Ueber das Hydrobenzamid'; Ann. Chim. Phys. 1836, 62, 23. It is noteworthy that as early as in 1865 Reinecke and Beilstein reported the preparation of benzylidenaminophenylacetonitrile (sic!) in the reaction of hydrobenzamide with hydrogen cyanide: (b) Reinecke, A.; Beilstein, F. Ann. Chem. 1865, 136, 173. In the Beilstein data base (Beilstein Informationssysteme GmbH; BS9804PR) 88 substances related to hydrobenzamide and 318 of their reactions were recorded. For recent examples see: (c) Karupaiyan, K.; Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron Lett. 1997, 38, 4281-4284; (d) Larter, M. L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R.; Walsh, P. J. Tetrahedron Lett. 1998, 39, 4785-4788; (e) Kupfer, R.; Brinker, U. H. J. Org. Chem. 1996, 61, 4185-4186; (f) Kayukov, Ya. S.; Nasakin, O. E.; Urman, Ya. G.; Khrustalev, N. V.; Nesterov, V. N.; Antipin, M. Y.; Lyshchikov, A. N.; Lukin, P. M. Khim. Geterotsikl. Soedin. 1996, 32, 1395; (g) Nasakin, O. E.; Lyshchikov, A. N.; Lukin, P. M.; Bulaj, A. Kh. Khim. Geterotsikl. Soedin. 1994, 30, 353; (h) Rey, A. W.; Droghini, R.; Douglas, J. L.; Vemishetti, P.; Boettger, S. D.; Racha, S.; Dillon, J. L. Can. J. Chem. 1994, 72, 2131; (i) Levai, L.; Bozsing, D.; Benko, P.; Lax, G.; Mikite, G. Synth. Commun. 1992, 22, 47; (j) Goerlitzer, K.; Schmidt, E. Arch. Pharm. (Weinheim) 1991, 324, 785. The preparation of hydrobenzamide is also described in (k) Vogel, A. I. A Text-book of Practical Organic Chemistry, 3rd ed.; Longmans, Green & Co. Ltd: London, 1961; pp. 735 (Polish Edition 1964, WNT Warszawa).
51. Hydrobenzamide was described for the first time in 1836 by Laurent in the reaction of benzaldehyde ('Bittermandel öl') with gaseous ammonia: (a) Laurent, M. A. Ann. Pharm. 1837, 21, 130-134; 'Ueber das Hydrobenzamid'; Ann. Chim. Phys. 1836, 62, 23. It is noteworthy that as early as in 1865 Reinecke and Beilstein reported the preparation of benzylidenaminophenylacetonitrile (sic!) in the reaction of hydrobenzamide with hydrogen cyanide: (b) Reinecke, A.; Beilstein, F. Ann. Chem. 1865, 136, 173. In the Beilstein data base (Beilstein Informationssysteme GmbH; BS9804PR) 88 substances related to hydrobenzamide and 318 of their reactions were recorded. For recent examples see: (c) Karupaiyan, K.; Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron Lett. 1997, 38, 4281-4284; (d) Larter, M. L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R.; Walsh, P. J. Tetrahedron Lett. 1998, 39, 4785-4788; (e) Kupfer, R.; Brinker, U. H. J. Org. Chem. 1996, 61, 4185-4186; (f) Kayukov, Ya. S.; Nasakin, O. E.; Urman, Ya. G.; Khrustalev, N. V.; Nesterov, V. N.; Antipin, M. Y.; Lyshchikov, A. N.; Lukin, P. M. Khim. Geterotsikl. Soedin. 1996, 32, 1395; (g) Nasakin, O. E.; Lyshchikov, A. N.; Lukin, P. M.; Bulaj, A. Kh. Khim. Geterotsikl. Soedin. 1994, 30, 353; (h) Rey, A. W.; Droghini, R.; Douglas, J. L.; Vemishetti, P.; Boettger, S. D.; Racha, S.; Dillon, J. L. Can. J. Chem. 1994, 72, 2131; (i) Levai, L.; Bozsing, D.; Benko, P.; Lax, G.; Mikite, G. Synth. Commun. 1992, 22, 47; (j) Goerlitzer, K.; Schmidt, E. Arch. Pharm. (Weinheim) 1991, 324, 785. The preparation of hydrobenzamide is also described in (k) Vogel, A. I. A Text-book of Practical Organic Chemistry, 3rd ed.; Longmans, Green & Co. Ltd: London, 1961; pp. 735 (Polish Edition 1964, WNT Warszawa).
52. Hydrobenzamide was described for the first time in 1836 by Laurent in the reaction of benzaldehyde ('Bittermandel öl') with gaseous ammonia: (a) Laurent, M. A. Ann. Pharm. 1837, 21, 130-134; 'Ueber das Hydrobenzamid'; Ann. Chim. Phys. 1836, 62, 23. It is noteworthy that as early as in 1865 Reinecke and Beilstein reported the preparation of benzylidenaminophenylacetonitrile (sic!) in the reaction of hydrobenzamide with hydrogen cyanide: (b) Reinecke, A.; Beilstein, F. Ann. Chem. 1865, 136, 173. In the Beilstein data base (Beilstein Informationssysteme GmbH; BS9804PR) 88 substances related to hydrobenzamide and 318 of their reactions were recorded. For recent examples see: (c) Karupaiyan, K.; Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron Lett. 1997, 38, 4281-4284; (d) Larter, M. L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R.; Walsh, P. J. Tetrahedron Lett. 1998, 39, 4785-4788; (e) Kupfer, R.; Brinker, U. H. J. Org. Chem. 1996, 61, 4185-4186; (f) Kayukov, Ya. S.; Nasakin, O. E.; Urman, Ya. G.; Khrustalev, N. V.; Nesterov, V. N.; Antipin, M. Y.; Lyshchikov, A. N.; Lukin, P. M. Khim. Geterotsikl. Soedin. 1996, 32, 1395; (g) Nasakin, O. E.; Lyshchikov, A. N.; Lukin, P. M.; Bulaj, A. Kh. Khim. Geterotsikl. Soedin. 1994, 30, 353; (h) Rey, A. W.; Droghini, R.; Douglas, J. L.; Vemishetti, P.; Boettger, S. D.; Racha, S.; Dillon, J. L. Can. J. Chem. 1994, 72, 2131; (i) Levai, L.; Bozsing, D.; Benko, P.; Lax, G.; Mikite, G. Synth. Commun. 1992, 22, 47; (j) Goerlitzer, K.; Schmidt, E. Arch. Pharm. (Weinheim) 1991, 324, 785. The preparation of hydrobenzamide is also described in (k) Vogel, A. I. A Text-book of Practical Organic Chemistry, 3rd ed.; Longmans, Green & Co. Ltd: London, 1961; pp. 735 (Polish Edition 1964, WNT Warszawa).
53. Hydrobenzamide was described for the first time in 1836 by Laurent in the reaction of benzaldehyde ('Bittermandel öl') with gaseous ammonia: (a) Laurent, M. A. Ann. Pharm. 1837, 21, 130-134; 'Ueber das Hydrobenzamid'; Ann. Chim. Phys. 1836, 62, 23. It is noteworthy that as early as in 1865 Reinecke and Beilstein reported the preparation of benzylidenaminophenylacetonitrile (sic!) in the reaction of hydrobenzamide with hydrogen cyanide: (b) Reinecke, A.; Beilstein, F. Ann. Chem. 1865, 136, 173. In the Beilstein data base (Beilstein Informationssysteme GmbH; BS9804PR) 88 substances related to hydrobenzamide and 318 of their reactions were recorded. For recent examples see: (c) Karupaiyan, K.; Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron Lett. 1997, 38, 4281-4284; (d) Larter, M. L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R.; Walsh, P. J. Tetrahedron Lett. 1998, 39, 4785-4788; (e) Kupfer, R.; Brinker, U. H. J. Org. Chem. 1996, 61, 4185-4186; (f) Kayukov, Ya. S.; Nasakin, O. E.; Urman, Ya. G.; Khrustalev, N. V.; Nesterov, V. N.; Antipin, M. Y.; Lyshchikov, A. N.; Lukin, P. M. Khim. Geterotsikl. Soedin. 1996, 32, 1395; (g) Nasakin, O. E.; Lyshchikov, A. N.; Lukin, P. M.; Bulaj, A. Kh. Khim. Geterotsikl. Soedin. 1994, 30, 353; (h) Rey, A. W.; Droghini, R.; Douglas, J. L.; Vemishetti, P.; Boettger, S. D.; Racha, S.; Dillon, J. L. Can. J. Chem. 1994, 72, 2131; (i) Levai, L.; Bozsing, D.; Benko, P.; Lax, G.; Mikite, G. Synth. Commun. 1992, 22, 47; (j) Goerlitzer, K.; Schmidt, E. Arch. Pharm. (Weinheim) 1991, 324, 785. The preparation of hydrobenzamide is also described in (k) Vogel, A. I. A Text-book of Practical Organic Chemistry, 3rd ed.; Longmans, Green & Co. Ltd: London, 1961; pp. 735 (Polish Edition 1964, WNT Warszawa).
54. Hydrobenzamide was described for the first time in 1836 by Laurent in the reaction of benzaldehyde ('Bittermandel öl') with gaseous ammonia: (a) Laurent, M. A. Ann. Pharm. 1837, 21, 130-134; 'Ueber das Hydrobenzamid'; Ann. Chim. Phys. 1836, 62, 23. It is noteworthy that as early as in 1865 Reinecke and Beilstein reported the preparation of benzylidenaminophenylacetonitrile (sic!) in the reaction of hydrobenzamide with hydrogen cyanide: (b) Reinecke, A.; Beilstein, F. Ann. Chem. 1865, 136, 173. In the Beilstein data base (Beilstein Informationssysteme GmbH; BS9804PR) 88 substances related to hydrobenzamide and 318 of their reactions were recorded. For recent examples see: (c) Karupaiyan, K.; Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron Lett. 1997, 38, 4281-4284; (d) Larter, M. L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R.; Walsh, P. J. Tetrahedron Lett. 1998, 39, 4785-4788; (e) Kupfer, R.; Brinker, U. H. J. Org. Chem. 1996, 61, 4185-4186; (f) Kayukov, Ya. S.; Nasakin, O. E.; Urman, Ya. G.; Khrustalev, N. V.; Nesterov, V. N.; Antipin, M. Y.; Lyshchikov, A. N.; Lukin, P. M. Khim. Geterotsikl. Soedin. 1996, 32, 1395; (g) Nasakin, O. E.; Lyshchikov, A. N.; Lukin, P. M.; Bulaj, A. Kh. Khim. Geterotsikl. Soedin. 1994, 30, 353; (h) Rey, A. W.; Droghini, R.; Douglas, J. L.; Vemishetti, P.; Boettger, S. D.; Racha, S.; Dillon, J. L. Can. J. Chem. 1994, 72, 2131; (i) Levai, L.; Bozsing, D.; Benko, P.; Lax, G.; Mikite, G. Synth. Commun. 1992, 22, 47; (j) Goerlitzer, K.; Schmidt, E. Arch. Pharm. (Weinheim) 1991, 324, 785. The preparation of hydrobenzamide is also described in (k) Vogel, A. I. A Text-book of Practical Organic Chemistry, 3rd ed.; Longmans, Green & Co. Ltd: London, 1961; pp. 735 (Polish Edition 1964, WNT Warszawa).
55. Hydrobenzamide was described for the first time in 1836 by Laurent in the reaction of benzaldehyde ('Bittermandel öl') with gaseous ammonia: (a) Laurent, M. A. Ann. Pharm. 1837, 21, 130-134; 'Ueber das Hydrobenzamid'; Ann. Chim. Phys. 1836, 62, 23. It is noteworthy that as early as in 1865 Reinecke and Beilstein reported the preparation of benzylidenaminophenylacetonitrile (sic!) in the reaction of hydrobenzamide with hydrogen cyanide: (b) Reinecke, A.; Beilstein, F. Ann. Chem. 1865, 136, 173. In the Beilstein data base (Beilstein Informationssysteme GmbH; BS9804PR) 88 substances related to hydrobenzamide and 318 of their reactions were recorded. For recent examples see: (c) Karupaiyan, K.; Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron Lett. 1997, 38, 4281-4284; (d) Larter, M. L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R.; Walsh, P. J. Tetrahedron Lett. 1998, 39, 4785-4788; (e) Kupfer, R.; Brinker, U. H. J. Org. Chem. 1996, 61, 4185-4186; (f) Kayukov, Ya. S.; Nasakin, O. E.; Urman, Ya. G.; Khrustalev, N. V.; Nesterov, V. N.; Antipin, M. Y.; Lyshchikov, A. N.; Lukin, P. M. Khim. Geterotsikl. Soedin. 1996, 32, 1395; (g) Nasakin, O. E.; Lyshchikov, A. N.; Lukin, P. M.; Bulaj, A. Kh. Khim. Geterotsikl. Soedin. 1994, 30, 353; (h) Rey, A. W.; Droghini, R.; Douglas, J. L.; Vemishetti, P.; Boettger, S. D.; Racha, S.; Dillon, J. L. Can. J. Chem. 1994, 72, 2131; (i) Levai, L.; Bozsing, D.; Benko, P.; Lax, G.; Mikite, G. Synth. Commun. 1992, 22, 47; (j) Goerlitzer, K.; Schmidt, E. Arch. Pharm. (Weinheim) 1991, 324, 785. The preparation of hydrobenzamide is also described in (k) Vogel, A. I. A Text-book of Practical Organic Chemistry, 3rd ed.; Longmans, Green & Co. Ltd: London, 1961; pp. 735 (Polish Edition 1964, WNT Warszawa).
56. Hydrobenzamide was described for the first time in 1836 by Laurent in the reaction of benzaldehyde ('Bittermandel öl') with gaseous ammonia: (a) Laurent, M. A. Ann. Pharm. 1837, 21, 130-134; 'Ueber das Hydrobenzamid'; Ann. Chim. Phys. 1836, 62, 23. It is noteworthy that as early as in 1865 Reinecke and Beilstein reported the preparation of benzylidenaminophenylacetonitrile (sic!) in the reaction of hydrobenzamide with hydrogen cyanide: (b) Reinecke, A.; Beilstein, F. Ann. Chem. 1865, 136, 173. In the Beilstein data base (Beilstein Informationssysteme GmbH; BS9804PR) 88 substances related to hydrobenzamide and 318 of their reactions were recorded. For recent examples see: (c) Karupaiyan, K.; Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron Lett. 1997, 38, 4281-4284; (d) Larter, M. L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R.; Walsh, P. J. Tetrahedron Lett. 1998, 39, 4785-4788; (e) Kupfer, R.; Brinker, U. H. J. Org. Chem. 1996, 61, 4185-4186; (f) Kayukov, Ya. S.; Nasakin, O. E.; Urman, Ya. G.; Khrustalev, N. V.; Nesterov, V. N.; Antipin, M. Y.; Lyshchikov, A. N.; Lukin, P. M. Khim. Geterotsikl. Soedin. 1996, 32, 1395; (g) Nasakin, O. E.; Lyshchikov, A. N.; Lukin, P. M.; Bulaj, A. Kh. Khim. Geterotsikl. Soedin. 1994, 30, 353; (h) Rey, A. W.; Droghini, R.; Douglas, J. L.; Vemishetti, P.; Boettger, S. D.; Racha, S.; Dillon, J. L. Can. J. Chem. 1994, 72, 2131; (i) Levai, L.; Bozsing, D.; Benko, P.; Lax, G.; Mikite, G. Synth. Commun. 1992, 22, 47; (j) Goerlitzer, K.; Schmidt, E. Arch. Pharm. (Weinheim) 1991, 324, 785. The preparation of hydrobenzamide is also described in (k) Vogel, A. I. A Text-book of Practical Organic Chemistry, 3rd ed.; Longmans, Green & Co. Ltd: London, 1961; pp. 735 (Polish Edition 1964, WNT Warszawa).
57. Hydrobenzamide was described for the first time in 1836 by Laurent in the reaction of benzaldehyde ('Bittermandel öl') with gaseous ammonia: (a) Laurent, M. A. Ann. Pharm. 1837, 21, 130-134; 'Ueber das Hydrobenzamid'; Ann. Chim. Phys. 1836, 62, 23. It is noteworthy that as early as in 1865 Reinecke and Beilstein reported the preparation of benzylidenaminophenylacetonitrile (sic!) in the reaction of hydrobenzamide with hydrogen cyanide: (b) Reinecke, A.; Beilstein, F. Ann. Chem. 1865, 136, 173. In the Beilstein data base (Beilstein Informationssysteme GmbH; BS9804PR) 88 substances related to hydrobenzamide and 318 of their reactions were recorded. For recent examples see: (c) Karupaiyan, K.; Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron Lett. 1997, 38, 4281-4284; (d) Larter, M. L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R.; Walsh, P. J. Tetrahedron Lett. 1998, 39, 4785-4788; (e) Kupfer, R.; Brinker, U. H. J. Org. Chem. 1996, 61, 4185-4186; (f) Kayukov, Ya. S.; Nasakin, O. E.; Urman, Ya. G.; Khrustalev, N. V.; Nesterov, V. N.; Antipin, M. Y.; Lyshchikov, A. N.; Lukin, P. M. Khim. Geterotsikl. Soedin. 1996, 32, 1395; (g) Nasakin, O. E.; Lyshchikov, A. N.; Lukin, P. M.; Bulaj, A. Kh. Khim. Geterotsikl. Soedin. 1994, 30, 353; (h) Rey, A. W.; Droghini, R.; Douglas, J. L.; Vemishetti, P.; Boettger, S. D.; Racha, S.; Dillon, J. L. Can. J. Chem. 1994, 72, 2131; (i) Levai, L.; Bozsing, D.; Benko, P.; Lax, G.; Mikite, G. Synth. Commun. 1992, 22, 47; (j) Goerlitzer, K.; Schmidt, E. Arch. Pharm. (Weinheim) 1991, 324, 785. The preparation of hydrobenzamide is also described in (k) Vogel, A. I. A Text-book of Practical Organic Chemistry, 3rd ed.; Longmans, Green & Co. Ltd: London, 1961; pp. 735 (Polish Edition 1964, WNT Warszawa).
58. Hydrobenzamide was described for the first time in 1836 by Laurent in the reaction of benzaldehyde ('Bittermandel öl') with gaseous ammonia: (a) Laurent, M. A. Ann. Pharm. 1837, 21, 130-134; 'Ueber das Hydrobenzamid'; Ann. Chim. Phys. 1836, 62, 23. It is noteworthy that as early as in 1865 Reinecke and Beilstein reported the preparation of benzylidenaminophenylacetonitrile (sic!) in the reaction of hydrobenzamide with hydrogen cyanide: (b) Reinecke, A.; Beilstein, F. Ann. Chem. 1865, 136, 173. In the Beilstein data base (Beilstein Informationssysteme GmbH; BS9804PR) 88 substances related to hydrobenzamide and 318 of their reactions were recorded. For recent examples see: (c) Karupaiyan, K.; Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron Lett. 1997, 38, 4281-4284; (d) Larter, M. L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R.; Walsh, P. J. Tetrahedron Lett. 1998, 39, 4785-4788; (e) Kupfer, R.; Brinker, U. H. J. Org. Chem. 1996, 61, 4185-4186; (f) Kayukov, Ya. S.; Nasakin, O. E.; Urman, Ya. G.; Khrustalev, N. V.; Nesterov, V. N.; Antipin, M. Y.; Lyshchikov, A. N.; Lukin, P. M. Khim. Geterotsikl. Soedin. 1996, 32, 1395; (g) Nasakin, O. E.; Lyshchikov, A. N.; Lukin, P. M.; Bulaj, A. Kh. Khim. Geterotsikl. Soedin. 1994, 30, 353; (h) Rey, A. W.; Droghini, R.; Douglas, J. L.; Vemishetti, P.; Boettger, S. D.; Racha, S.; Dillon, J. L. Can. J. Chem. 1994, 72, 2131; (i) Levai, L.; Bozsing, D.; Benko, P.; Lax, G.; Mikite, G. Synth. Commun. 1992, 22, 47; (j) Goerlitzer, K.; Schmidt, E. Arch. Pharm. (Weinheim) 1991, 324, 785. The preparation of hydrobenzamide is also described in (k) Vogel, A. I. A Text-book of Practical Organic Chemistry, 3rd ed.; Longmans, Green & Co. Ltd: London, 1961; pp. 735 (Polish Edition 1964, WNT Warszawa).
59. Hydrobenzamide was described for the first time in 1836 by Laurent in the reaction of benzaldehyde ('Bittermandel öl') with gaseous ammonia: (a) Laurent, M. A. Ann. Pharm. 1837, 21, 130-134; 'Ueber das Hydrobenzamid'; Ann. Chim. Phys. 1836, 62, 23. It is noteworthy that as early as in 1865 Reinecke and Beilstein reported the preparation of benzylidenaminophenylacetonitrile (sic!) in the reaction of hydrobenzamide with hydrogen cyanide: (b) Reinecke, A.; Beilstein, F. Ann. Chem. 1865, 136, 173. In the Beilstein data base (Beilstein Informationssysteme GmbH; BS9804PR) 88 substances related to hydrobenzamide and 318 of their reactions were recorded. For recent examples see: (c) Karupaiyan, K.; Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron Lett. 1997, 38, 4281-4284; (d) Larter, M. L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R.; Walsh, P. J. Tetrahedron Lett. 1998, 39, 4785-4788; (e) Kupfer, R.; Brinker, U. H. J. Org. Chem. 1996, 61, 4185-4186; (f) Kayukov, Ya. S.; Nasakin, O. E.; Urman, Ya. G.; Khrustalev, N. V.; Nesterov, V. N.; Antipin, M. Y.; Lyshchikov, A. N.; Lukin, P. M. Khim. Geterotsikl. Soedin. 1996, 32, 1395; (g) Nasakin, O. E.; Lyshchikov, A. N.; Lukin, P. M.; Bulaj, A. Kh. Khim. Geterotsikl. Soedin. 1994, 30, 353; (h) Rey, A. W.; Droghini, R.; Douglas, J. L.; Vemishetti, P.; Boettger, S. D.; Racha, S.; Dillon, J. L. Can. J. Chem. 1994, 72, 2131; (i) Levai, L.; Bozsing, D.; Benko, P.; Lax, G.; Mikite, G. Synth. Commun. 1992, 22, 47; (j) Goerlitzer, K.; Schmidt, E. Arch. Pharm. (Weinheim) 1991, 324, 785. The preparation of hydrobenzamide is also described in (k) Vogel, A. I. A Text-book of Practical Organic Chemistry, 3rd ed.; Longmans, Green & Co. Ltd: London, 1961; pp. 735 (Polish Edition 1964, WNT Warszawa).
60. Hydrobenzamide was described for the first time in 1836 by Laurent in the reaction of benzaldehyde ('Bittermandel öl') with gaseous ammonia: (a) Laurent, M. A. Ann. Pharm. 1837, 21, 130-134; 'Ueber das Hydrobenzamid'; Ann. Chim. Phys. 1836, 62, 23. It is noteworthy that as early as in 1865 Reinecke and Beilstein reported the preparation of benzylidenaminophenylacetonitrile (sic!) in the reaction of hydrobenzamide with hydrogen cyanide: (b) Reinecke, A.; Beilstein, F. Ann. Chem. 1865, 136, 173. In the Beilstein data base (Beilstein Informationssysteme GmbH; BS9804PR) 88 substances related to hydrobenzamide and 318 of their reactions were recorded. For recent examples see: (c) Karupaiyan, K.; Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron Lett. 1997, 38, 4281-4284; (d) Larter, M. L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R.; Walsh, P. J. Tetrahedron Lett. 1998, 39, 4785-4788; (e) Kupfer, R.; Brinker, U. H. J. Org. Chem. 1996, 61, 4185-4186; (f) Kayukov, Ya. S.; Nasakin, O. E.; Urman, Ya. G.; Khrustalev, N. V.; Nesterov, V. N.; Antipin, M. Y.; Lyshchikov, A. N.; Lukin, P. M. Khim. Geterotsikl. Soedin. 1996, 32, 1395; (g) Nasakin, O. E.; Lyshchikov, A. N.; Lukin, P. M.; Bulaj, A. Kh. Khim. Geterotsikl. Soedin. 1994, 30, 353; (h) Rey, A. W.; Droghini, R.; Douglas, J. L.; Vemishetti, P.; Boettger, S. D.; Racha, S.; Dillon, J. L. Can. J. Chem. 1994, 72, 2131; (i) Levai, L.; Bozsing, D.; Benko, P.; Lax, G.; Mikite, G. Synth. Commun. 1992, 22, 47; (j) Goerlitzer, K.; Schmidt, E. Arch. Pharm. (Weinheim) 1991, 324, 785. The preparation of hydrobenzamide is also described in (k) Vogel, A. I. A Text-book of Practical Organic Chemistry, 3rd ed.; Longmans, Green & Co. Ltd: London, 1961; pp. 735 (Polish Edition 1964, WNT Warszawa).
61. Hydrobenzamide was described for the first time in 1836 by Laurent in the reaction of benzaldehyde ('Bittermandel öl') with gaseous ammonia: (a) Laurent, M. A. Ann. Pharm. 1837, 21, 130-134; 'Ueber das Hydrobenzamid'; Ann. Chim. Phys. 1836, 62, 23. It is noteworthy that as early as in 1865 Reinecke and Beilstein reported the preparation of benzylidenaminophenylacetonitrile (sic!) in the reaction of hydrobenzamide with hydrogen cyanide: (b) Reinecke, A.; Beilstein, F. Ann. Chem. 1865, 136, 173. In the Beilstein data base (Beilstein Informationssysteme GmbH; BS9804PR) 88 substances related to hydrobenzamide and 318 of their reactions were recorded. For recent examples see: (c) Karupaiyan, K.; Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron Lett. 1997, 38, 4281-4284; (d) Larter, M. L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R.; Walsh, P. J. Tetrahedron Lett. 1998, 39, 4785-4788; (e) Kupfer, R.; Brinker, U. H. J. Org. Chem. 1996, 61, 4185-4186; (f) Kayukov, Ya. S.; Nasakin, O. E.; Urman, Ya. G.; Khrustalev, N. V.; Nesterov, V. N.; Antipin, M. Y.; Lyshchikov, A. N.; Lukin, P. M. Khim. Geterotsikl. Soedin. 1996, 32, 1395; (g) Nasakin, O. E.; Lyshchikov, A. N.; Lukin, P. M.; Bulaj, A. Kh. Khim. Geterotsikl. Soedin. 1994, 30, 353; (h) Rey, A. W.; Droghini, R.; Douglas, J. L.; Vemishetti, P.; Boettger, S. D.; Racha, S.; Dillon, J. L. Can. J. Chem. 1994, 72, 2131; (i) Levai, L.; Bozsing, D.; Benko, P.; Lax, G.; Mikite, G. Synth. Commun. 1992, 22, 47; (j) Goerlitzer, K.; Schmidt, E. Arch. Pharm. (Weinheim) 1991, 324, 785. The preparation of hydrobenzamide is also described in (k) Vogel, A. I. A Text-book of Practical Organic Chemistry, 3rd ed.; Longmans, Green & Co. Ltd: London, 1961; pp. 735 (Polish Edition 1964, WNT Warszawa).
62. In fact, the reaction of hydrobenzamides and diethyl phosphite was also reported in the literature: (a) Kreutzkamp, N.; Cordes, G. Liebigs Ann. Chem. 1959, 623, 103; (b) Rogozhin, S. V.; Davankov, V. A.; Belov, Yu. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1973, 955; (c) Belov, Yu. P.; Rakhnovich, G. B.; Davankov, V. A.; Godovikov, N. N.; Aleksandrov, G. G.; Struchkov, Ju. T. Izv. Akad. Nauk SSSR, Ser. Khim. 1980, 1125; (d) Pudovik, A. N.; Shagidullin, R. R.; Khairullin, V. K.; Vandyukova, I. I.; Chernova, A. V.; Gainullin, R. M.; Pudovik, M. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1996, 1303; (e) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877.
63. In fact, the reaction of hydrobenzamides and diethyl phosphite was also reported in the literature: (a) Kreutzkamp, N.; Cordes, G. Liebigs Ann. Chem. 1959, 623, 103; (b) Rogozhin, S. V.; Davankov, V. A.; Belov, Yu. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1973, 955; (c) Belov, Yu. P.; Rakhnovich, G. B.; Davankov, V. A.; Godovikov, N. N.; Aleksandrov, G. G.; Struchkov, Ju. T. Izv. Akad. Nauk SSSR, Ser. Khim. 1980, 1125; (d) Pudovik, A. N.; Shagidullin, R. R.; Khairullin, V. K.; Vandyukova, I. I.; Chernova, A. V.; Gainullin, R. M.; Pudovik, M. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1996, 1303; (e) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877.
64. In fact, the reaction of hydrobenzamides and diethyl phosphite was also reported in the literature: (a) Kreutzkamp, N.; Cordes, G. Liebigs Ann. Chem. 1959, 623, 103; (b) Rogozhin, S. V.; Davankov, V. A.; Belov, Yu. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1973, 955; (c) Belov, Yu. P.; Rakhnovich, G. B.; Davankov, V. A.; Godovikov, N. N.; Aleksandrov, G. G.; Struchkov, Ju. T. Izv. Akad. Nauk SSSR, Ser. Khim. 1980, 1125; (d) Pudovik, A. N.; Shagidullin, R. R.; Khairullin, V. K.; Vandyukova, I. I.; Chernova, A. V.; Gainullin, R. M.; Pudovik, M. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1996, 1303; (e) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877.
65. In fact, the reaction of hydrobenzamides and diethyl phosphite was also reported in the literature: (a) Kreutzkamp, N.; Cordes, G. Liebigs Ann. Chem. 1959, 623, 103; (b) Rogozhin, S. V.; Davankov, V. A.; Belov, Yu. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1973, 955; (c) Belov, Yu. P.; Rakhnovich, G. B.; Davankov, V. A.; Godovikov, N. N.; Aleksandrov, G. G.; Struchkov, Ju. T. Izv. Akad. Nauk SSSR, Ser. Khim. 1980, 1125; (d) Pudovik, A. N.; Shagidullin, R. R.; Khairullin, V. K.; Vandyukova, I. I.; Chernova, A. V.; Gainullin, R. M.; Pudovik, M. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1996, 1303; (e) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877.
66. In fact, the reaction of hydrobenzamides and diethyl phosphite was also reported in the literature: (a) Kreutzkamp, N.; Cordes, G. Liebigs Ann. Chem. 1959, 623, 103; (b) Rogozhin, S. V.; Davankov, V. A.; Belov, Yu. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1973, 955; (c) Belov, Yu. P.; Rakhnovich, G. B.; Davankov, V. A.; Godovikov, N. N.; Aleksandrov, G. G.; Struchkov, Ju. T. Izv. Akad. Nauk SSSR, Ser. Khim. 1980, 1125; (d) Pudovik, A. N.; Shagidullin, R. R.; Khairullin, V. K.; Vandyukova, I. I.; Chernova, A. V.; Gainullin, R. M.; Pudovik, M. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1996, 1303; (e) Gross, H.; Beisert, S.; Costisella, B. J. Prakt. Chem. 1981, 323, 877.
67. 3b).