Synthesis of selenol esters via selenium-assisted carbonylation of 2-arylpropionitriles with carbon monoxide

Synthesis

Volumn , Issue 3, 1997, Pages 342-346

  Maeda, Hajime ^a   Fujiwara, Shin Ichi ^b   Nishiyama, Akira ^a   Shin Ike, Tsutomu ^b   Kambe, Nobuaki ^a   Sonoda, Noboru ^a  

^a OSAKA UNIVERSITY   (Japan)

^b OSAKA DENTAL UNIVERSITY   (Japan)

Author keywords

2 arylpropionitrile; carbon monoxide; carbonylation; selenium; selenol ester

Indexed keywords

ORGANOSELENIUM DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030908521     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1185     Document Type: Article

References (81)

1. For recent reviews, see: (a) Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, pp 461-484. (b) Ogawa, A.; Sonoda, N. In Comprehensive Organic Functional Group Transformations, Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon; Oxford, 1995; Vol. 5, pp 231-255.
2. For recent reviews, see: (a) Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, pp 461-484. (b) Ogawa, A.; Sonoda, N. In Comprehensive Organic Functional Group Transformations, Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon; Oxford, 1995; Vol. 5, pp 231-255.
3. For leading references, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1989, 54, 1777. (d) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (e) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429.
4. For leading references, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1989, 54, 1777. (d) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (e) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429.
5. For leading references, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1989, 54, 1777. (d) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (e) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429.
6. For leading references, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1989, 54, 1777. (d) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (e) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429.
7. For leading references, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1989, 54, 1777. (d) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (e) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429.
8. (a) Kozikowski, A. P.; Ames, A. J. Am. Chem. Soc. 1980, 102, 860.
9. (b) Kozikowski, A. P.; Ames, A. Tetrahedron 1985, 41, 4821.
10. (a) Kozikowski, A. P.; Ames, A. J. Org. Chem. 1978, 43, 2735.
11. (b) Dabdoub, M. J.; Viana, L. H. Synth. Commun. 1992, 22, 1619.
12. (a) Back, T. G.; Kerr, R. G. Tetrahedron Lett. 1982, 23, 3241.
13. (b) Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4355.
14. (c) Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4359.
15. Back, T. G.; Kerr, R. G. Tetrahedron 1985, 41, 4759.
16. Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N. Organometallics 1992, 11, 3937.
17. Petasis, N. A.; Lu, S.-P. Tetrahedron Lett. 1995, 36, 2393.
18. (a) Ishihara, H.; Hirabayashi, Y. Chem. Lett. 1976, 203.
19. (b) Ishihara, H.; Sato, S.; Hirabayashi, Y. Bull. Chem. Soc. Jpn. 1977, 50, 3007.
20. (c) Ishihara, H.; Muto, S.; Kato, S. Synthesis 1986, 128.
21. (d) Nishiyama, Y.; Katsuura, A.; Negoro, A.; Hamanaka, S.; Miyoshi, N.; Yamana, Y.; Ogawa, A.; Sonoda, N. J. Org. Chem. 1991, 56, 3776.
22. (e) Kojima, Y.; Ibi, K.; Kanda, T.; Ishihara, H.; Murai, T.; Kato, S. Bull. Chem. Soc. Jpn. 1993, 66, 990.
23. For leading references, see: (a) Renson, M.; Draguet, C. Bull. Soc. Chim. Belg. 1962, 71, 260. (b) Hiscock, S. M.; Swann, D. A.; Turnbull, J. H. J. Chem. Soc., Sect. D 1970, 1310. (c) Derkach, N. Y.; Tishchenko, N. P. Zh. Org. Khim. 1977, 13, 100; Chem. Abstr. 1977, 86, 155314. (d) Mullen, G. P.; Luthra, N. P.; Dunlap, R. B.; Odom, J. D. J. Org. Chem. 1985, 50, 811. (e) Testaferri, L.; Tiecco, M.; Tingoli, M.; Chianelli, D. Tetrahedron 1986, 42, 4577.
24. For leading references, see: (a) Renson, M.; Draguet, C. Bull. Soc. Chim. Belg. 1962, 71, 260. (b) Hiscock, S. M.; Swann, D. A.; Turnbull, J. H. J. Chem. Soc., Sect. D 1970, 1310. (c) Derkach, N. Y.; Tishchenko, N. P. Zh. Org. Khim. 1977, 13, 100; Chem. Abstr. 1977, 86, 155314. (d) Mullen, G. P.; Luthra, N. P.; Dunlap, R. B.; Odom, J. D. J. Org. Chem. 1985, 50, 811. (e) Testaferri, L.; Tiecco, M.; Tingoli, M.; Chianelli, D. Tetrahedron 1986, 42, 4577.
25. For leading references, see: (a) Renson, M.; Draguet, C. Bull. Soc. Chim. Belg. 1962, 71, 260. (b) Hiscock, S. M.; Swann, D. A.; Turnbull, J. H. J. Chem. Soc., Sect. D 1970, 1310. (c) Derkach, N. Y.; Tishchenko, N. P. Zh. Org. Khim. 1977, 13, 100; Chem. Abstr. 1977, 86, 155314. (d) Mullen, G. P.; Luthra, N. P.; Dunlap, R. B.; Odom, J. D. J. Org. Chem. 1985, 50, 811. (e) Testaferri, L.; Tiecco, M.; Tingoli, M.; Chianelli, D. Tetrahedron 1986, 42, 4577.
26. For leading references, see: (a) Renson, M.; Draguet, C. Bull. Soc. Chim. Belg. 1962, 71, 260. (b) Hiscock, S. M.; Swann, D. A.; Turnbull, J. H. J. Chem. Soc., Sect. D 1970, 1310. (c) Derkach, N. Y.; Tishchenko, N. P. Zh. Org. Khim. 1977, 13, 100; Chem. Abstr. 1977, 86, 155314. (d) Mullen, G. P.; Luthra, N. P.; Dunlap, R. B.; Odom, J. D. J. Org. Chem. 1985, 50, 811. (e) Testaferri, L.; Tiecco, M.; Tingoli, M.; Chianelli, D. Tetrahedron 1986, 42, 4577.
27. For leading references, see: (a) Renson, M.; Draguet, C. Bull. Soc. Chim. Belg. 1962, 71, 260. (b) Hiscock, S. M.; Swann, D. A.; Turnbull, J. H. J. Chem. Soc., Sect. D 1970, 1310. (c) Derkach, N. Y.; Tishchenko, N. P. Zh. Org. Khim. 1977, 13, 100; Chem. Abstr. 1977, 86, 155314. (d) Mullen, G. P.; Luthra, N. P.; Dunlap, R. B.; Odom, J. D. J. Org. Chem. 1985, 50, 811. (e) Testaferri, L.; Tiecco, M.; Tingoli, M.; Chianelli, D. Tetrahedron 1986, 42, 4577.
28. For leading references, see: (a) Renson, M.; Draguet, C. Bull. Soc. Chim. Belg. 1962, 71, 260. (b) Hiscock, S. M.; Swann, D. A.; Turnbull, J. H. J. Chem. Soc., Sect. D 1970, 1310. (c) Derkach, N. Y.; Tishchenko, N. P. Zh. Org. Khim. 1977, 13, 100; Chem. Abstr. 1977, 86, 155314. (d) Mullen, G. P.; Luthra, N. P.; Dunlap, R. B.; Odom, J. D. J. Org. Chem. 1985, 50, 811. (e) Testaferri, L.; Tiecco, M.; Tingoli, M.; Chianelli, D. Tetrahedron 1986, 42, 4577.
29. (a) Sviridov, A. F.; Ermolenko, M. S.; Yashunskii, D. V.; Kochetkov, N. K. Izv. Akad. Nauk SSSR. Ser. Khim. 1985, 1650; Chem. Abstr. 1986, 104, 186033.
30. (a) Sviridov, A. F.; Ermolenko, M. S.; Yashunskii, D. V.; Kochetkov, N. K. Izv. Akad. Nauk SSSR. Ser. Khim. 1985, 1650; Chem. Abstr. 1986, 104, 186033.
31. (b) Sviridov, A. F.; Ermolenko, M. S.; Yashunskii, D. V.; Kochetkov, N. K. Irz. Akad. Nauk SSSR, Ser. Khim. 1985, 1654; Chem. Abstr. 1987, 107, 77274.
32. (b) Sviridov, A. F.; Ermolenko, M. S.; Yashunskii, D. V.; Kochetkov, N. K. Irz. Akad. Nauk SSSR, Ser. Khim. 1985, 1654; Chem. Abstr. 1987, 107, 77274.
33. (c) Inoue, T.; Takeda, T.; Kambe, N.; Ogawa, A.; Ryu, I.; Sonoda, N. J. Org. Chem. 1994, 59, 5824.
34. (a) Grieco, P. A.; Yokoyama, Y.; Williams, E. J. Org. Chem. 1978, 43, 1283.
35. (b) Grieco, P. A.; Jaw, J. Y.; Claremon, D. A.; Nicolaou, K. C. J. Org. Chem. 1981, 46, 1215.
36. (c) Tomoda, S.; Takeuchi, Y.; Nomura, Y. Synthesis 1985, 212.
37. (d) Nicolaou, K. C.; Petasis, N. A.; Claremon, D. A. Tetrahedron 1985, 41, 4835.
38. (e) Batty, D.; Crich, D. Synthesis 1990, 273.
39. (a) Takahashi, H.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1987, 334, C43.
40. (b) Uemura, S.; Takahashi, H.; Ohe, K.; Sugita, N. J. Organomet. Chem. 1989, 361, 63.
41. (c) Kuniyasu, H.; Ogawa, A.; Miyazaki, S.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 9796.
42. Back, T. G.; Collins, S. Tetrahedron Lett. 1979, 2661.
43. Kato, S.; Kabuto, H.; Ishihara, H.; Murai, T. Synthesis 1985, 520.
44. Ishihara, H.; Matsunami, N.; Yamada, Y. Synthesis 1987, 371.
45. Hoshi, M.; Masuda, Y.; Arase, A. Bull. Chem. Soc. Jpn. 1988, 61, 3764.
46. Hewkin, C. T.; Jackson, R.F.W.; Clegg, W. J. Chem. Soc., Perkin Trans, 1 1991, 3091.
47. Kanda, T.; Mizoguchi, K.; Koike, T.; Murai, T.; Kato, S. J. Chem. Soc., Chem. Commun. 1993, 1631.
48. (a) Kondo, K.; Takarada, M.; Murai, S.; Sonoda, N. Synthesis 1979, 597.
49. (b) Fujiwara, S.; Miyoshi, N.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Phys. Org. Chem. 1989, 2, 359.
50. Maeda, H.; Fujiwara, S.; Shin-Ike, T.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 8160.
51. For carbonylation of haloacetonitriles: (a) Suzuki, T.; Matsuki, T.; Kudo, K.; Sugita, N. Nippon Kagaku Kaishi 1983, 1482; Chem. Abstr. 1984, 100, 33956. (b) Yasuda, K.; Shinoda, K. Bull. Chem. Soc. Jpn. 1992, 65, 289. (c) Lapidus, A. L.; Pirozhkov, S. D.; Tumanova, A. R.; Koksharova, T. G.; Volkova, N. V.; Bakukev, V. A.; Mokrushin, V. S. Khim. Tverd. Topl. (Moscow) 1993, 5; Chem. Abstr. 1993, 119, 75050. Ramirez-Vega, F.; Laurent, P.; Clement, J.-C.; Abbayes, H. J. Mol. Catal. A: Chem. 1995, 96, 15.
52. For carbonylation of haloacetonitriles: (a) Suzuki, T.; Matsuki, T.; Kudo, K.; Sugita, N. Nippon Kagaku Kaishi 1983, 1482; Chem. Abstr. 1984, 100, 33956. (b) Yasuda, K.; Shinoda, K. Bull. Chem. Soc. Jpn. 1992, 65, 289. (c) Lapidus, A. L.; Pirozhkov, S. D.; Tumanova, A. R.; Koksharova, T. G.; Volkova, N. V.; Bakukev, V. A.; Mokrushin, V. S. Khim. Tverd. Topl. (Moscow) 1993, 5; Chem. Abstr. 1993, 119, 75050. Ramirez-Vega, F.; Laurent, P.; Clement, J.-C.; Abbayes, H. J. Mol. Catal. A: Chem. 1995, 96, 15.
53. For carbonylation of haloacetonitriles: (a) Suzuki, T.; Matsuki, T.; Kudo, K.; Sugita, N. Nippon Kagaku Kaishi 1983, 1482; Chem. Abstr. 1984, 100, 33956. (b) Yasuda, K.; Shinoda, K. Bull. Chem. Soc. Jpn. 1992, 65, 289. (c) Lapidus, A. L.; Pirozhkov, S. D.; Tumanova, A. R.; Koksharova, T. G.; Volkova, N. V.; Bakukev, V. A.; Mokrushin, V. S. Khim. Tverd. Topl. (Moscow) 1993, 5; Chem. Abstr. 1993, 119, 75050. Ramirez-Vega, F.; Laurent, P.; Clement, J.-C.; Abbayes, H. J. Mol. Catal. A: Chem. 1995, 96, 15.
54. For carbonylation of haloacetonitriles: (a) Suzuki, T.; Matsuki, T.; Kudo, K.; Sugita, N. Nippon Kagaku Kaishi 1983, 1482; Chem. Abstr. 1984, 100, 33956. (b) Yasuda, K.; Shinoda, K. Bull. Chem. Soc. Jpn. 1992, 65, 289. (c) Lapidus, A. L.; Pirozhkov, S. D.; Tumanova, A. R.; Koksharova, T. G.; Volkova, N. V.; Bakukev, V. A.; Mokrushin, V. S. Khim. Tverd. Topl. (Moscow) 1993, 5; Chem. Abstr. 1993, 119, 75050. Ramirez-Vega, F.; Laurent, P.; Clement, J.-C.; Abbayes, H. J. Mol. Catal. A: Chem. 1995, 96, 15.
55. For carbonylation of haloacetonitriles: (a) Suzuki, T.; Matsuki, T.; Kudo, K.; Sugita, N. Nippon Kagaku Kaishi 1983, 1482; Chem. Abstr. 1984, 100, 33956. (b) Yasuda, K.; Shinoda, K. Bull. Chem. Soc. Jpn. 1992, 65, 289. (c) Lapidus, A. L.; Pirozhkov, S. D.; Tumanova, A. R.; Koksharova, T. G.; Volkova, N. V.; Bakukev, V. A.; Mokrushin, V. S. Khim. Tverd. Topl. (Moscow) 1993, 5; Chem. Abstr. 1993, 119, 75050. Ramirez-Vega, F.; Laurent, P.; Clement, J.-C.; Abbayes, H. J. Mol. Catal. A: Chem. 1995, 96, 15.
56. For carbonylation of haloacetonitriles: (a) Suzuki, T.; Matsuki, T.; Kudo, K.; Sugita, N. Nippon Kagaku Kaishi 1983, 1482; Chem. Abstr. 1984, 100, 33956. (b) Yasuda, K.; Shinoda, K. Bull. Chem. Soc. Jpn. 1992, 65, 289. (c) Lapidus, A. L.; Pirozhkov, S. D.; Tumanova, A. R.; Koksharova, T. G.; Volkova, N. V.; Bakukev, V. A.; Mokrushin, V. S. Khim. Tverd. Topl. (Moscow) 1993, 5; Chem. Abstr. 1993, 119, 75050. Ramirez-Vega, F.; Laurent, P.; Clement, J.-C.; Abbayes, H. J. Mol. Catal. A: Chem. 1995, 96, 15.
57. For carbonylation of benzyl halides: (a) Schoenberg, A.; Bartoletti, I.; Heck, R. F. J. Org. Chem. 1974, 39, 3318.
58. (b) Stille, J. K.; Wong, P. K. J. Org. Chem. 1975, 40, 532.
59. Alper, H.; Hashem, K.; Heveling, J. Organometallics 1982, 1, 775.
60. Rosario, R.; Stuhl, L. S. Tetrahedron Lett. 1982, 23, 3999.
61. (e) Tanguy, G.; Weinberger, B.; Abbayes, H. Tetrahedron Lett. 1983, 24, 4005.
62. (f) Satyanarayana, N.; Periasamy, M. Tetrahedron Lett. 1987, 28, 2633.
63. For hydroformylation and hydroesterification of acrylonitrile: (a) Matsuda, A. Bull. Chem. Soc. Jpn. 1967, 40, 135. (b) Matsuda, A. Tokyo Kogyo Shikensho Hokoku 1980, 75. 419; Chem. Abstr. 1981, 95, 80071. (c) Murata, K.; Matsuda, A. Kagaku Gijutsu Kenkyusho Hokoku 1984, 79, 149; Chem. Abstr. 1984, 101, 191108.
64. For hydroformylation and hydroesterification of acrylonitrile: (a) Matsuda, A. Bull. Chem. Soc. Jpn. 1967, 40, 135. (b) Matsuda, A. Tokyo Kogyo Shikensho Hokoku 1980, 75. 419; Chem. Abstr. 1981, 95, 80071. (c) Murata, K.; Matsuda, A. Kagaku Gijutsu Kenkyusho Hokoku 1984, 79, 149; Chem. Abstr. 1984, 101, 191108.
65. For hydroformylation and hydroesterification of acrylonitrile: (a) Matsuda, A. Bull. Chem. Soc. Jpn. 1967, 40, 135. (b) Matsuda, A. Tokyo Kogyo Shikensho Hokoku 1980, 75. 419; Chem. Abstr. 1981, 95, 80071. (c) Murata, K.; Matsuda, A. Kagaku Gijutsu Kenkyusho Hokoku 1984, 79, 149; Chem. Abstr. 1984, 101, 191108.
66. For hydroformylation and hydroesterification of acrylonitrile: (a) Matsuda, A. Bull. Chem. Soc. Jpn. 1967, 40, 135. (b) Matsuda, A. Tokyo Kogyo Shikensho Hokoku 1980, 75. 419; Chem. Abstr. 1981, 95, 80071. (c) Murata, K.; Matsuda, A. Kagaku Gijutsu Kenkyusho Hokoku 1984, 79, 149; Chem. Abstr. 1984, 101, 191108.
67. For hydroformylation and hydroesterification of acrylonitrile: (a) Matsuda, A. Bull. Chem. Soc. Jpn. 1967, 40, 135. (b) Matsuda, A. Tokyo Kogyo Shikensho Hokoku 1980, 75. 419; Chem. Abstr. 1981, 95, 80071. (c) Murata, K.; Matsuda, A. Kagaku Gijutsu Kenkyusho Hokoku 1984, 79, 149; Chem. Abstr. 1984, 101, 191108.
68. For hydroformylation of styrenes: (a) Ungváry, F.; Markó, L. Organometallics 1982, 1, 1120. (b) Brown, J.M.; Kent, A.G. J. Chem. Soc., Parkin Trans. 2 1987, 1597. (c) Amer, I.; Alper, H. J. Am. Chem. Soc. 1990, 112, 3674. (d) Miyazawa, M.; Momose, S.; Yamamoto, K. Synlett 1990, 711. (e) Abu-Gnim, C.; Amer, I. J. Chem. Soc., Chem. Commun. 1994, 115
69. For hydroformylation of styrenes: (a) Ungváry, F.; Markó, L. Organometallics 1982, 1, 1120. (b) Brown, J.M.; Kent, A.G. J. Chem. Soc., Parkin Trans. 2 1987, 1597. (c) Amer, I.; Alper, H. J. Am. Chem. Soc. 1990, 112, 3674. (d) Miyazawa, M.; Momose, S.; Yamamoto, K. Synlett 1990, 711. (e) Abu-Gnim, C.; Amer, I. J. Chem. Soc., Chem. Commun. 1994, 115
70. For hydroformylation of styrenes: (a) Ungváry, F.; Markó, L. Organometallics 1982, 1, 1120. (b) Brown, J.M.; Kent, A.G. J. Chem. Soc., Parkin Trans. 2 1987, 1597. (c) Amer, I.; Alper, H. J. Am. Chem. Soc. 1990, 112, 3674. (d) Miyazawa, M.; Momose, S.; Yamamoto, K. Synlett 1990, 711. (e) Abu-Gnim, C.; Amer, I. J. Chem. Soc., Chem. Commun. 1994, 115
71. For hydroformylation of styrenes: (a) Ungváry, F.; Markó, L. Organometallics 1982, 1, 1120. (b) Brown, J.M.; Kent, A.G. J. Chem. Soc., Parkin Trans. 2 1987, 1597. (c) Amer, I.; Alper, H. J. Am. Chem. Soc. 1990, 112, 3674. (d) Miyazawa, M.; Momose, S.; Yamamoto, K. Synlett 1990, 711. (e) Abu-Gnim, C.; Amer, I. J. Chem. Soc., Chem. Commun. 1994, 115
72. For hydroformylation of styrenes: (a) Ungváry, F.; Markó, L. Organometallics 1982, 1, 1120. (b) Brown, J.M.; Kent, A.G. J. Chem. Soc., Parkin Trans. 2 1987, 1597. (c) Amer, I.; Alper, H. J. Am. Chem. Soc. 1990, 112, 3674. (d) Miyazawa, M.; Momose, S.; Yamamoto, K. Synlett 1990, 711. (e) Abu-Gnim, C.; Amer, I. J. Chem. Soc., Chem. Commun. 1994, 115
73. (a) Porta, F.; Ragaini, F.; Cenini, S.; Demartin, F. Organometallics 1990, 9, 929.
74. (b) Belderraín, T. R.; Knight, D. A.; Irvine, D.J.; Pancque, M.; Poveda, M. L.; Carmona, E. J. Chem. Soc., Dalton Trans. 1992, 1491.
75. (a) Nagy-Magos, Z.; Bor, G.; Markó, L. J. Organomet. Chem. 1968, 14, 205.
76. (b) Craig, P. J.; Green, M. J. Chem. Soc., Sect. A 1969, 157.
77. (c) Fachinetti, G.; Fochi, G.; Floriani, C. J. Chem. Soc., Dalton Trans. 1977, 1946.
78. (d) Cawse, J. N.; Fiato, R. A.; Pruett, R. L. J. Organomet. Chem. 1979, 172, 405.
79. (e) Cotton, J. D.; Crisp, G.T.; Daly, V.A. Inorg. Chim. Acta 1981, 47, 165.
80. (f) Sonnenberger, D.C.; Mintz, E. A.; Marks, T.J. J. Am. Chem. Soc. 1984, 106, 3484.
81. (g) Cotton, J. D.; Kroes, M. M.; Markwell, R. D.; Miles, E. A. J. Organomet. Chem. 1990, 388, 133.