N-(Arylsulfonyl)trihaloacetimidoyl Chlorides and Their Reactions with Phosphites

European Journal of Organic Chemistry

Volumn , Issue 21, 2003, Pages 4181-4186

  Rassukana, Yuliya V ^a   Onys'Ko, Petro P ^a   Grechukha, Anatolii G ^a   Sinitsa, Anatolii D ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

Author keywords

Phosphorylation; Schiff bases; Sulfonamides; Synthetic design; Umpolung

Indexed keywords

1 SULFONYLAMINO 1 CHLOROTRIFLUOROETHYL PHOSPHONATE; CHLORIDE; N (SULFONYL)TRIHALOACETIMIDOYL CHLORIDE; N ACYLSULFONAMIDE; N SULFONYL N TRICHLOROVINYL PHOSPHORAMIDATE; PHOSPHITE; SCHIFF BASE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0344014178     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300275     Document Type: Article

References (39)

1. [1a] K. Uneyama, J. Fluor. Chem. 1999, 97, 11-25.
2. [1b] K. Tamura, H. Mizukami, K. Maeda, H. Watanabe, K. Uneyama, J. Org. Chem. 1993, 58, 32-35.
3. [1c] O. A. Sinitsa, N. V. Kolotilo, P. P. Onys'ko, Ukr. Khim. Zh. 1998, 64, 47-66 [Ukr. Chem. J. 1998, 64, 43-61 (Engl. Transl.)].
4. [1c] O. A. Sinitsa, N. V. Kolotilo, P. P. Onys'ko, Ukr. Khim. Zh. 1998, 64, 47-66 [Ukr. Chem. J. 1998, 64, 43-61 (Engl. Transl.)].
5. [2a] P. P. Onys'ko, A. A. Sinitsa, V. V. Pirozhenko, A. N. Chernega, Heteroatom Chem. 2002, 13, 22-26.
6. [2b] Yu. V. Rassukana, Ya. A. Sizonenko, A. A. Sinitsa, V. I. Boiko, A. A. Podoprigorina, P. P. Onys'ko, Zh. Obshch. Khim. 2002, 72, 1798-1801.
7. [3a] P. P. Onys'ko, A. D. Sinitsa, N. V. Kolotylo, E. A. Suvalova, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 147, 381.
8. [3b] P. P. Onys'ko, A. A. Sinitsa, N. V. Kolotylo, Main Group Chem. News 1997, 5, 27-28.
9. [3c] P. P. Onys'ko, Russ. J. Gen. Chem. 1999, 69, 153-154.
10. [3d] V. I. Boiko, A. A. Sinitsa, P. P. Onys'ko, Russ. J. Gen. Chem. 1999, 69, 1879-1882.
11. [3e] P. P. Onys'ko, A. A. Sinitsa, Yu. V. Rassukana, Ya. A. Sizonenko, A. D. Sinitsa, Abstr., Int. Conf on Phosphorus Chem. Sendai, 2001, PA108.
12. S. N. Osipov, O. I. Artyushin, A. F. Kolomiets, Mendeleev Commun. 2000, 192-193.
13. Organic Compounds in Medicinal Chemistry and Biomedicinal Applications, (Eds: R. Filler, Y. Kobayashi, L. M. Yagupolskii), Elsevier, Amsterdam, 1993. B. Xu, S. Zhu, Heteroatom Chem. 1997, 8, 309-315.
14. Organic Compounds in Medicinal Chemistry and Biomedicinal Applications, (Eds: R. Filler, Y. Kobayashi, L. M. Yagupolskii), Elsevier, Amsterdam, 1993. B. Xu, S. Zhu, Heteroatom Chem. 1997, 8, 309-315.
15. [6a] H. W. Roesky, H. H. Giere, Chem. Ber. 1969, 102, 3707-3712.
16. [6b] H. W. Roesky, H. H. Giere, D. P. Babb, Inorg. Chem. 1970, 9, 1076-1079.
17. P. P. Onys'ko, O. A. Suvalova, Yu. V. Rassukana, T. I. Chudakova, A. D. Sinitsa, Tetrahedron Lett. 2003, 44, 1855-1857.
18. [8a] A. D. Sinitsa, K. S. Krishtal, V. I. Kal'chenko, Zh. Obshch. Khim. 1980, 50, 465-466.
19. [8b] A. D. Sinitsa, T. V. Kolodka, A. K. Shurubura, Zh. Obshch. Khim. 1987, 57, 475-477.
20. [8c] W. Huang, Y. Zhang, C. Yuan, Phosphorus, Sulfur, Silicon Relat. Elem. 1995, 107, 21-26. C. Yuan, Y. Zhang, Heteroatom Chem. 2002, 13, 22-26.
21. [8c] W. Huang, Y. Zhang, C. Yuan, Phosphorus, Sulfur, Silicon Relat. Elem. 1995, 107, 21-26. C. Yuan, Y. Zhang, Heteroatom Chem. 2002, 13, 22-26.
22. P. P. Onys'ko, T. V. Kolodka, A. A. Kudryavtsev, A. D. Sinitsa, Zh. Obshch. Khim. 1993, 63, 1562-1566. P. P. Onys'ko, T. V. Kolodka, N. V. Kolotylo, A. A. Kudryavtsev, A. D. Sinitsa, Zh. Obshch. Khim. 1994, 64, 396-402.
23. P. P. Onys'ko, T. V. Kolodka, A. A. Kudryavtsev, A. D. Sinitsa, Zh. Obshch. Khim. 1993, 63, 1562-1566. P. P. Onys'ko, T. V. Kolodka, N. V. Kolotylo, A. A. Kudryavtsev, A. D. Sinitsa, Zh. Obshch. Khim. 1994, 64, 396-402.
24. N. V. Kolotilo, A. A. Sinitsa, P. P. Onys'ko, Russ. J. Gen. Chem. 1997, 67, 154-155.
25. Yu. V. Rassukana, K. O. Davydova, P. P. Onys'ko, A. D. Sinitsa, J. Fluor. Chem. 2002, 117, 107-113.
26. C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165-195.
27. N. V. Kolotilo, A. D. Sinitsa, P. P. Onys'ko, Zh. Obshch. Khim. 1994, 64, 1304-1305.
28. K. Afarinkia, C. W. Rees, J. I. G. Cadogan, Tetrahedron 1990, 46, 7175-7196.
29. P. P. Onys'ko, T. V. Kolodka, A. D. Sinitsa, Zh. Obshch. Khim. 1995, 65, 948-954.
30. N. V. Kolotilo, A. A. Sinitsa, P. P. Onys'ko, Zh. Obshch. Khim. 1995, 65, 1221-1222.
31. Only one example of unphosphorylated difluorovinylsulfonamides has been reported so far. See: Yu. V. Zeifman, Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 202-205.
32. B. S. Drach, V. S. Brovarets, O. S. Smolii, Syntheses of Nitrogen-Containing Heterocyclic Compounds on the Basis of Amidoalkylating Agents (in Russian), Naukova Dumka, Kiev, 1992.
33. A. D. Sinitsa, T. V. Kim, E. I. Kiseleva, P. P. Onys'ko, Phosphorus, Sulfur, Silicon Relat. Elem. 2002, 177, 2055.
34. G. Russel, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 793-820. F. H. Ebetino, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 9-12. L. Widler, K. A. Jaeggi, J. R. Green, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 5-8. J. Mönkkönen, N. Makkonen, M. J. Rogers, J. C. Frith, S. Auriola, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 321-324.
35. G. Russel, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 793-820. F. H. Ebetino, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 9-12. L. Widler, K. A. Jaeggi, J. R. Green, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 5-8. J. Mönkkönen, N. Makkonen, M. J. Rogers, J. C. Frith, S. Auriola, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 321-324.
36. G. Russel, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 793-820. F. H. Ebetino, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 9-12. L. Widler, K. A. Jaeggi, J. R. Green, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 5-8. J. Mönkkönen, N. Makkonen, M. J. Rogers, J. C. Frith, S. Auriola, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 321-324.
37. G. Russel, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 793-820. F. H. Ebetino, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 9-12. L. Widler, K. A. Jaeggi, J. R. Green, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 5-8. J. Mönkkönen, N. Makkonen, M. J. Rogers, J. C. Frith, S. Auriola, Phosphorus, Sulfur, Silicon Relat. Elem. 1999, 144-146, 321-324.
38. A. D. Sinitsa, N. A. Parkhomenko, L. N. Markovskii, Zh. Obshch. Khim. 1983, 53, 354-359.
39. V. A. Nikolaev, P. Yu. Utkin, I. K. Korobitsyna, Zh. Org. Khim. 1989, 25, 1176-1179.