Intramolecular assistance of electron transfer. Oxidative cleavage of the carbon-tin bond of tetraalkylstannanes

Journal of the American Chemical Society

Volumn 119, Issue 40, 1997, Pages 9361-9365

  Yoshida, Jun Ichi ^a   Izawa, Mitsuhiko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOTIN COMPOUND;

ARTICLE; CHEMICAL BINDING; ELECTROCHEMISTRY; ELECTRON TRANSPORT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION POTENTIAL; REACTION ANALYSIS;

EID: 0030780513     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970899t     Document Type: Article

References (29)

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7. Synthetic utility of electron transfer induced bond cleavage of group 14 metal compounds. For example, photoelectron transfer reactions: (a) Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 1992, 25, 233-240. (b) Mizuno, K.; Ikeda, M.; Toda, S.; Otsuji, Y. J. Am. Chem. Soc. 1988, 110, 1288-1290. Electrochemical reactions: (c) Yoshida, J. Top. Current Chem. 1994, 170, 40-81. (d) Yoshida, J.; Ishichi, Y.; Isoe, S. J. Am. Chem. Soc. 1992, 114, 7594-7595. Chemical electron transfer reactions: (e) Narasaka, K.; Kohno, Y. Bull. Chem. Soc. Jpn. 1993, 66, 3456-3463 and references cited therein.
8. Synthetic utility of electron transfer induced bond cleavage of group 14 metal compounds. For example, photoelectron transfer reactions: (a) Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 1992, 25, 233-240. (b) Mizuno, K.; Ikeda, M.; Toda, S.; Otsuji, Y. J. Am. Chem. Soc. 1988, 110, 1288-1290. Electrochemical reactions: (c) Yoshida, J. Top. Current Chem. 1994, 170, 40-81. (d) Yoshida, J.; Ishichi, Y.; Isoe, S. J. Am. Chem. Soc. 1992, 114, 7594-7595. Chemical electron transfer reactions: (e) Narasaka, K.; Kohno, Y. Bull. Chem. Soc. Jpn. 1993, 66, 3456-3463 and references cited therein.
9. Synthetic utility of electron transfer induced bond cleavage of group 14 metal compounds. For example, photoelectron transfer reactions: (a) Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 1992, 25, 233-240. (b) Mizuno, K.; Ikeda, M.; Toda, S.; Otsuji, Y. J. Am. Chem. Soc. 1988, 110, 1288-1290. Electrochemical reactions: (c) Yoshida, J. Top. Current Chem. 1994, 170, 40-81. (d) Yoshida, J.; Ishichi, Y.; Isoe, S. J. Am. Chem. Soc. 1992, 114, 7594-7595. Chemical electron transfer reactions: (e) Narasaka, K.; Kohno, Y. Bull. Chem. Soc. Jpn. 1993, 66, 3456-3463 and references cited therein.
10. Synthetic utility of electron transfer induced bond cleavage of group 14 metal compounds. For example, photoelectron transfer reactions: (a) Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 1992, 25, 233-240. (b) Mizuno, K.; Ikeda, M.; Toda, S.; Otsuji, Y. J. Am. Chem. Soc. 1988, 110, 1288-1290. Electrochemical reactions: (c) Yoshida, J. Top. Current Chem. 1994, 170, 40-81. (d) Yoshida, J.; Ishichi, Y.; Isoe, S. J. Am. Chem. Soc. 1992, 114, 7594-7595. Chemical electron transfer reactions: (e) Narasaka, K.; Kohno, Y. Bull. Chem. Soc. Jpn. 1993, 66, 3456-3463 and references cited therein.
11. Synthetic utility of electron transfer induced bond cleavage of group 14 metal compounds. For example, photoelectron transfer reactions: (a) Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 1992, 25, 233-240. (b) Mizuno, K.; Ikeda, M.; Toda, S.; Otsuji, Y. J. Am. Chem. Soc. 1988, 110, 1288-1290. Electrochemical reactions: (c) Yoshida, J. Top. Current Chem. 1994, 170, 40-81. (d) Yoshida, J.; Ishichi, Y.; Isoe, S. J. Am. Chem. Soc. 1992, 114, 7594-7595. Chemical electron transfer reactions: (e) Narasaka, K.; Kohno, Y. Bull. Chem. Soc. Jpn. 1993, 66, 3456-3463 and references cited therein.
12. The organotin compounds having a carbonyl group at the β-position are called tin homoenolates. See, for example, Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis: Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, Chapter 1.14, pp 441-454.
13. (a) Corriu, R. J. P.; Young, J. C. In The Chemistry of Organic Silicon Compound; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1989; Part 2, Chapter 20, pp 1241-1288.
14. (b) Kumada, M.; Tamao, K.; Yoshida, J. J. Organomet. Chem. 1982, 239, 115-132 and references cited therein.
15. -1, respectively: Kuivila, H. G.; Dixon, J. E.; Maxfield, P. L.; Scarpa, N. M.; Topka, T. M.; Tsai, K.-H.; Wursthorn, K. R. J. Organomet. Chem. 1975, 86, 89-107.
16. Facilitation of electrophilic reactions of tetraorganostannane by the carbonyl coordination has been reported. See ref 7 and: Podesta, J. C.; Chopa, A. B.; Koll. L. C. J. Chem. Res. (S) 1986, 308-309.
17. Nagao and Ochiai reported the effective intramolecular coordination of acetal oxygen to tin although an electronegative chlorine atom is present on the tin: Ochiai, M.; Iwaki, S.; Ukita, T.; Matsuura, Y.; Shiro, M.; Nagao, Y. J. Am. Chem. Soc. 1988, 110, 4606-4610.
18. It has been reported that the oxidative cleavage of the carbon-tin bond gives the carbocation and the tin radical if the electron donating group is attached on the carbon. Eaton, D. F. J. Am. Chem. Soc. 1980, 102, 3278-3281.
19. The abstract of halogen atom from organic halides by tin radicals is well-known. For example, see: Curran, D. P.; Jasperse, C. P.; Totleben, M. J. J. Org. Chem. 1991, 56, 7169-7172. See also ref 9.
20. For example, Eaton, D. F. Pure Appl. Chem, 1984, 56, 1191-1202.
21. Intramolecular coordination of a nitrogen atom at tin promoting the C-Sn bond cleavage has been reported. For example: (a) Vedejs, E.; Haight, A. R.; Moss, W. O. J. Am. Chem. Soc. 1992, 114, 6556-6558. (b) Jousseaume, B.; Villeneuve, P. J. Chem. Soc., Chem. Commun. 1987, 513-514.
22. Intramolecular coordination of a nitrogen atom at tin promoting the C-Sn bond cleavage has been reported. For example: (a) Vedejs, E.; Haight, A. R.; Moss, W. O. J. Am. Chem. Soc. 1992, 114, 6556-6558. (b) Jousseaume, B.; Villeneuve, P. J. Chem. Soc., Chem. Commun. 1987, 513-514.
23. 15
24. Mahon, M. F.; Molloy, K. C.; Waterfield, P. C. Organometallics 1993, 12, 769-774.
25. Davies, A. G. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 2, Chapter 11, pp 519-628.
26. The coordination of the pyridyl group to tin in [2-(2-pyridyl)ethyl]-diphenyltin halides has been reported. See ref 17.
27. *) were local minima according to the vibration analysis. The calculations from ECP (HF/LANL2DZ) also gave similar optimized structures.
28. MNDO calculations of tetraaikyltin cation radical indicated that the bond to the apical alkyl group is lengthened by ca. 13%. Dewar, M. J. S.; Grady, G. L.; Kuhn, D. R. Organometallics 1985, 4, 1041-1044.
29. Ryu, I.; Sonoda, N. Organometallics, 1990, 9, 277-280.