Allylation of Phosphorus, Arsenic, and Antimony Trihalides by Allylic Stannanes. Synthesis, Spectroscopic Characterization, and Quantum Chemical Investigations of Allylic Phosphines, Arsines, and Stibines

Journal of Organic Chemistry

Volumn 63, Issue 1, 1998, Pages 59-68

  Le Serre, Stéphanie ^a   Guillemin, Jean Claude ^a   Karpati, Tamás ^b   Soos, László ^b   Nyulászi, László ^b   Veszprémi, Tamás ^b  

^a UNIV RENNES   (France)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002607996     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971000t     Document Type: Article

References (75)

1. (a) Nyulászi, L.; Szieberth, D.; Csonka, G.; Réffy, J.; Heinicke, J.; Veszprémi, T. Struct. Chem. 1995, 6, 1-7.
2. (b) Nyulaszi, L.; Veszprémi, T.; Csonka, G.; Réffy, J.; Heinicke, J. J. Organomet. Chem. 1989, 373, 57-61.
3. (c) Veszprémi, T.; Nyulászi, L.; Réffy, J.; Heinicke, J. J. Phys. Chem. 1992, 96, 623-626.
4. (d) Gonbeau, D.; Lacombe, S.; Lasnes, M.; Ripoll, J.-L.; Pfister-Guillouzo, G. J. Am. Chem. Soc. 1988, 110, 2730-2735.
5. (e) Shade, C.; von Ragué Schleyer, P. J. Chem. Soc., Chem. Commun. 1987, 1399-1401.
6. (f) Métail, V.; Senio, A.; Lassalle, L.; Guillemin, J.-C.; Pfister-Guillouzo, G. Organometallics 1995, 14, 4732-4735.
7. Lambert, J. B. Tetrahedron 1990, 46, 2677-2689.
8. Bock, H.; Kaim, W. Acc. Chem. Res. 1982, 15, 9-17. Nyulászi, L.; Veszprémi, T.; Réffy, J. J. Organomet. Chem. 1993, 445, 29-34.
9. Bock, H.; Kaim, W. Acc. Chem. Res. 1982, 15, 9-17. Nyulászi, L.; Veszprémi, T.; Réffy, J. J. Organomet. Chem. 1993, 445, 29-34.
10. Weidner, U.; Schweig, A. Angew. Chem., Int. Ed. Engl. 1972, 11, 146-147. Schmidt, H.; Schweig, A.; Mathey, F.; Müller, G. Tetrahedron 1975, 31, 1287-1294. Schmidt, H.; Schweig, A.; Vermeer, H. J. Mol. Struct. 1977, 37, 93-104.
11. Weidner, U.; Schweig, A. Angew. Chem., Int. Ed. Engl. 1972, 11, 146-147. Schmidt, H.; Schweig, A.; Mathey, F.; Müller, G. Tetrahedron 1975, 31, 1287-1294. Schmidt, H.; Schweig, A.; Vermeer, H. J. Mol. Struct. 1977, 37, 93-104.
12. Weidner, U.; Schweig, A. Angew. Chem., Int. Ed. Engl. 1972, 11, 146-147. Schmidt, H.; Schweig, A.; Mathey, F.; Müller, G. Tetrahedron 1975, 31, 1287-1294. Schmidt, H.; Schweig, A.; Vermeer, H. J. Mol. Struct. 1977, 37, 93-104.
13. Lambert, J. B.; Zhao, Y. J. Am. Chem. Soc. 1996, 118, 3156-3167.
14. Zverev, V. V.; Villem, J.; Villem, N.; Liorber, B. G.; Kitaev, Yu. P. Z. Obsch. Khim. 1981, 51, 303-308.
15. Zverev, V. V.; Villem, Ya.; Ermolaeva, L. V.; Lisin, A. F. Dokl. Akad. Nauk USSR 1979, 246, 1368-1372.
16. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron Rep. No. 337, 1993, 49, 7395-7426.
17. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron Rep. No. 337, 1993, 49, 7395-7426.
18. Keck, G. E.; Andrus, M. B.; Castellino, S. J. Am. Chem. Soc. 1989, 111, 8136-8141.
19. Denmark, S. E.; Wilson, T.; Willson, T. M. J. Am. Chem. Soc. 1988, 110, 984-986.
20. Yamamoto, Y.; Yatagai, H.; Ishihara, Y.; Maeda, N.; Maruyama, K. Tetrahedron 1984, 40, 2239-2246.
21. (a) McNeill, A. H.; Thomas, E. J. Synthesis 1994, 322-334.
22. (b) Marshall, J. A.; Jablonowski, J. A.; Welmaker, G. S. J. Org. Chem. 1996, 61, 2904-2907.
23. Rolland, H.; Potin, P.; Majoral, J.-P.; Bertrand, G. Tetrahedron Lett. 1992, 33, 8095-8098.
24. The use of these compounds as Lewis acids as already been reported; see, for example: Puri, J. K.; Kaur, J.; Sharma, V.; Miller, J. M. Polyhedron 1983, 2, 1287-1295. Le Roux, C.; Mandrou, S.; Dubac, J. J. Org. Chem. 1996, 61, 3885-3887.
25. The use of these compounds as Lewis acids as already been reported; see, for example: Puri, J. K.; Kaur, J.; Sharma, V.; Miller, J. M. Polyhedron 1983, 2, 1287-1295. Le Roux, C.; Mandrou, S.; Dubac, J. J. Org. Chem. 1996, 61, 3885-3887.
26. Baumhardt, G. C. Engenharia e quim. 1953, 5, 10-11; Chem. Abstr. 1954, 48, 3833a.
27. Baumhardt, G. C. Engenharia e quim. 1953, 5, 10-11; Chem. Abstr. 1954, 48, 3833a.
28. Schwartz, W. T., Jr.; Post, H. W. J. Organomet. Chem. 1964, 2, 357-360.
29. Matarasso-Tchiroukhine, E; Cadiot, P. J. Organomet. Chem. 1976, 121, 155-164.
30. Gerard, F.; Miginiac, P. J. Organomet. Chem. 1976, 111, 17-30. Slutsky, J.; Kwart, H. J. Am. Chem. Soc. 1973, 95, 8678-8685. Ruppert, J. F.; White, J. D. J. Org. Chem. 1976, 41, 550-551.
31. Gerard, F.; Miginiac, P. J. Organomet. Chem. 1976, 111, 17-30. Slutsky, J.; Kwart, H. J. Am. Chem. Soc. 1973, 95, 8678-8685. Ruppert, J. F.; White, J. D. J. Org. Chem. 1976, 41, 550-551.
32. Gerard, F.; Miginiac, P. J. Organomet. Chem. 1976, 111, 17-30. Slutsky, J.; Kwart, H. J. Am. Chem. Soc. 1973, 95, 8678-8685. Ruppert, J. F.; White, J. D. J. Org. Chem. 1976, 41, 550-551.
33. Fricsh, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Peterson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Ciolowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Reploge, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision B.2; Gaussian, Inc.: Pittsburgh PA, 1995.
34. Binning, Jr. R. C.; Curtiss, L. A. J. Comput. Chem. 1990, 11, 1206-1216.
35. Veszprémi, T.; Zsombok, Gy. Magy. Kem. Foly. 1986, 92, 39.
36. Banks, C. K.; Morgan, J. F.; Clarck, R. L.; Hatlelid, E. B.; Kahler, F. H.; Paxton, H. W.; Cragoe, E.; Andres, R. J.; Elpern, B.; Coles, R. F.; Lawhead, J.; Hamilton, C. S. J. Am. Chem. Soc. 1947, 69 927-930.
37. Lassalle, L.; Legoupy, S.; Guillemin, J.-C. Inorg. Chem. 1995, 35, 5694-5697.
38. Kormachev, V. V., Vasil'eva, T. V.; Bryantsov, B. I.. Kukhtin, V. A. Z. Obshch Khim. 1976, 46, 1264-1268 (J. Gen. Chim. USSR 1976, 1244-1247).
39. Kormachev, V. V., Vasil'eva, T. V.; Bryantsov, B. I.. Kukhtin, V. A. Z. Obshch Khim. 1976, 46, 1264-1268 (J. Gen. Chim. USSR 1976, 1244-1247).
40. (a) Liorber, B. G.; Khammatova, Z. M.; Razumov, A. I.; Zykova, T. V.; Borisova, T. B. Z. Obshch Khim. 1968, 38, 878-883 (J. Gen. Chim. USSR 1968, 38, 843-847). Krivchum, M. N.; Sendyurev, M. V.; Ionin, B. I.; Petrov, A. A. Z. Obshch. Khim. 1990, 60, 2394-2395 (J. Gen. Chim. USSR 1991, 60, 2140-2141).
41. (a) Liorber, B. G.; Khammatova, Z. M.; Razumov, A. I.; Zykova, T. V.; Borisova, T. B. Z. Obshch Khim. 1968, 38, 878-883 (J. Gen. Chim. USSR 1968, 38, 843-847). Krivchum, M. N.; Sendyurev, M. V.; Ionin, B. I.; Petrov, A. A. Z. Obshch. Khim. 1990, 60, 2394-2395 (J. Gen. Chim. USSR 1991, 60, 2140-2141).
42. (a) Liorber, B. G.; Khammatova, Z. M.; Razumov, A. I.; Zykova, T. V.; Borisova, T. B. Z. Obshch Khim. 1968, 38, 878-883 (J. Gen. Chim. USSR 1968, 38, 843-847). Krivchum, M. N.; Sendyurev, M. V.; Ionin, B. I.; Petrov, A. A. Z. Obshch. Khim. 1990, 60, 2394-2395 (J. Gen. Chim. USSR 1991, 60, 2140-2141).
43. (a) Liorber, B. G.; Khammatova, Z. M.; Razumov, A. I.; Zykova, T. V.; Borisova, T. B. Z. Obshch Khim. 1968, 38, 878-883 (J. Gen. Chim. USSR 1968, 38, 843-847). Krivchum, M. N.; Sendyurev, M. V.; Ionin, B. I.; Petrov, A. A. Z. Obshch. Khim. 1990, 60, 2394-2395 (J. Gen. Chim. USSR 1991, 60, 2140-2141).
44. (b) Gaumont, A.-C.; Bourumeau, K.; Denis, J.-M.; Guenot, P. J. Organomet. Chem. 1994, 484, 9-12.
45. 3 has been proposed (ref 13). However we observed that the reaction can be performed in toluene without photolysis, in the presence of duroquinone or acrylonitrile. Thus an anionic process cannot be excluded.
46. Seyferth, D.; Stone, F. G. A. J. Am. Chem. Soc. 1957, 79, 515-517.
47. Guillemin, J.-C.; Lassalle, L. Organometallics 1994, 13, 1525-1527. Guillemin, J.-C.; Lassalle, L.; Dréan, P.; Wlodarczak, G; Demaison, J. J. Am. Chem. Soc. 1994, 116, 8930-8936.
48. Guillemin, J.-C.; Lassalle, L. Organometallics 1994, 13, 1525-1527. Guillemin, J.-C.; Lassalle, L.; Dréan, P.; Wlodarczak, G; Demaison, J. J. Am. Chem. Soc. 1994, 116, 8930-8936.
49. Childs, A. F.; Plant, S. G. P.; Tompsett, A. L. L.; Weeks, G. A. J. Chem. Soc. (London) 1948, 2180-2183; Kamai, G.; Belorossowa, O. N. Izv. Akad. SSSR Ser. Khim. 1947, 191-196; Chem. Abstr. 1948, 4133f. Pellon, P.; Himdi-Kabbab, S.; Rault, L; Tonnard, F.; Hamelin, J. Tetrahedron Lett. 1990, 31, 1147-1150. Some cyclopentadienyldihaloarsines have also been described: Jutzi, P.; Kuhn, M. Chem. Ber. 1974, 107, 1228-1234.
50. Childs, A. F.; Plant, S. G. P.; Tompsett, A. L. L.; Weeks, G. A. J. Chem. Soc. (London) 1948, 2180-2183; Kamai, G.; Belorossowa, O. N. Izv. Akad. SSSR Ser. Khim. 1947, 191-196; Chem. Abstr. 1948, 4133f. Pellon, P.; Himdi-Kabbab, S.; Rault, L; Tonnard, F.; Hamelin, J. Tetrahedron Lett. 1990, 31, 1147-1150. Some cyclopentadienyldihaloarsines have also been described: Jutzi, P.; Kuhn, M. Chem. Ber. 1974, 107, 1228-1234.
51. Childs, A. F.; Plant, S. G. P.; Tompsett, A. L. L.; Weeks, G. A. J. Chem. Soc. (London) 1948, 2180-2183; Kamai, G.; Belorossowa, O. N. Izv. Akad. SSSR Ser. Khim. 1947, 191-196; Chem. Abstr. 1948, 4133f. Pellon, P.; Himdi-Kabbab, S.; Rault, L; Tonnard, F.; Hamelin, J. Tetrahedron Lett. 1990, 31, 1147-1150. Some cyclopentadienyldihaloarsines have also been described: Jutzi, P.; Kuhn, M. Chem. Ber. 1974, 107, 1228-1234.
52. Childs, A. F.; Plant, S. G. P.; Tompsett, A. L. L.; Weeks, G. A. J. Chem. Soc. (London) 1948, 2180-2183; Kamai, G.; Belorossowa, O. N. Izv. Akad. SSSR Ser. Khim. 1947, 191-196; Chem. Abstr. 1948, 4133f. Pellon, P.; Himdi-Kabbab, S.; Rault, L; Tonnard, F.; Hamelin, J. Tetrahedron Lett. 1990, 31, 1147-1150. Some cyclopentadienyldihaloarsines have also been described: Jutzi, P.; Kuhn, M. Chem. Ber. 1974, 107, 1228-1234.
53. Childs, A. F.; Plant, S. G. P.; Tompsett, A. L. L.; Weeks, G. A. J. Chem. Soc. (London) 1948, 2180-2183; Kamai, G.; Belorossowa, O. N. Izv. Akad. SSSR Ser. Khim. 1947, 191-196; Chem. Abstr. 1948, 4133f. Pellon, P.; Himdi-Kabbab, S.; Rault, L; Tonnard, F.; Hamelin, J. Tetrahedron Lett. 1990, 31, 1147-1150. Some cyclopentadienyldihaloarsines have also been described: Jutzi, P.; Kuhn, M. Chem. Ber. 1974, 107, 1228-1234.
54. Similar experiments have already been reported to prepare α-unsaturated halostibines or stannanes: Legoupy, S.; Lassalle, L.; Guillemin, J.-C.; Metail, V.; Senio, A.; Pfister-Guillouzo, G. Inorg. Chem. 1995, 35, 1466-1471. Lassalle, L.; Janati, T.; Guillemin, J.-C. J. Chem. Soc., Chem. Commun. 1995, 699-700. Guillemin, J.-C.; Bellec, N.; Kiz-Szétsi, S.; Nyulászi, L.; Veszprémi, T. Inorg. Chem., 1996, 36, 6586-6591.
55. Similar experiments have already been reported to prepare α-unsaturated halostibines or stannanes: Legoupy, S.; Lassalle, L.; Guillemin, J.-C.; Metail, V.; Senio, A.; Pfister-Guillouzo, G. Inorg. Chem. 1995, 35, 1466-1471. Lassalle, L.; Janati, T.; Guillemin, J.-C. J. Chem. Soc., Chem. Commun. 1995, 699-700. Guillemin, J.-C.; Bellec, N.; Kiz-Szétsi, S.; Nyulászi, L.; Veszprémi, T. Inorg. Chem., 1996, 36, 6586-6591.
56. Similar experiments have already been reported to prepare α-unsaturated halostibines or stannanes: Legoupy, S.; Lassalle, L.; Guillemin, J.-C.; Metail, V.; Senio, A.; Pfister-Guillouzo, G. Inorg. Chem. 1995, 35, 1466-1471. Lassalle, L.; Janati, T.; Guillemin, J.-C. J. Chem. Soc., Chem. Commun. 1995, 699-700. Guillemin, J.-C.; Bellec, N.; Kiz-Szétsi, S.; Nyulászi, L.; Veszprémi, T. Inorg. Chem., 1996, 36, 6586-6591.
57. Voskuil, W.; Arens, J. F. Rec. Trav. Chim. (Pays-Bas) 1964, 83, 1301-1304.
58. Childs, R. F.; Mulholland, D. L.; Nixon, A. Can. J. Chem. 1982, 60, 801-808.
59. Singleton, D. A.; Waller, S. C.; Zhang, Z.; Frantz, D. E.; Leung, S.-W. J. Am. Chem. Soc. 1996, 118, 9986-9987. Le Serre, S.; Guillemin, J.-C. Organometallics Submitted for publication.
60. Singleton, D. A.; Waller, S. C.; Zhang, Z.; Frantz, D. E.; Leung, S.-W. J. Am. Chem. Soc. 1996, 118, 9986-9987. Le Serre, S.; Guillemin, J.-C. Organometallics Submitted for publication.
61. Morise, X.; Green, M. L. H.; McGowan, P. C.; Simpson, S. J. J. Chem. Soc., Dalton Trans. 1994, 871-878.
62. Rheingold, A. L.; Bellama, J. M. J. Organomet. Chem. 1975, 102, 437-444.
63. Cabioch, J.-L.; Denis, J.-M. J. Organomet. Chem. 1989, 377, 227-233.
64. Guillemin, J.-C., Savignac, P.; Denis, J.-M. Inorg. Chem. 1991, 30, 2170-2173.
65. Shay, R. H., Diel, B. N.; Schubert, D. M.; Norman, A. D. Inorg. Chem. 1988, 27, 2378-2382.
66. Lasnes, M.-C., Ripoll, J.-L.; Thuillier, A. J. Chem. Soc., Perkin Trans. 1988, 99-104.
67. Shaftenaar, G. MOLDEN 2.5; Chaos Camm Center, Nijmengen, The Netherlands, 1994.
68. Rotation about the P-C and As-C bonds requires small energies only, see ref 1a, 1d, 1e.
69. Guerra, M. J. Am. Chem. Soc. 1992, 114, 2077-2085.
70. Wiberg, K. E. Tetrahedron 1968, 24, 1083-1096.
71. Bader, R. F. W.; Slee, T. S.; Cremer, D.; Kraka, E. J. Am. Chem. Soc. 1983, 105, 5061-5068. Bader, R. W. F. Acc. Chem. Res 1985, 18, 9-15.
72. Bader, R. F. W.; Slee, T. S.; Cremer, D.; Kraka, E. J. Am. Chem. Soc. 1983, 105, 5061-5068. Bader, R. W. F. Acc. Chem. Res 1985, 18, 9-15.
73. Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S. Handbook of HeI Photoelectron Spectra of Fundamental Molecules; Japan Scientific Press: Tokyo, 1980.
74. Lappert, M. F.; Pedley, J. B.; Wilkins, B. T.; Stelzer, O.; Unger, E. J. J. Chem. Soc., Dalton 1975, 1207-1214.
75. Szepes, L.; Nagy, A.; Zanathy, L. PES, of organic derivatives of As, Sb and Bi. In The chemistry of organic arsenic, antimony and bismuth compounds; Patai S., Ed.; John Wiley & Sons: New York, 1994.