Allylstannylation of Alkenes via Radical Process

Synlett

Volumn 1996, Issue 6, 1996, Pages 555-556

  Miura, Katsukiyo ^a   Matsuda, Toshie ^a   Hondo, Takeshi ^a   Ito, Hajime ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002202114     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5501     Document Type: Article

References (12)

1. Radical Reactions. No. 27. For No. 26, see, Miura, K.; Itoh, D.; Hondo, T.; Hosomi, A. Tetrahedron Letters, 1994, 35, 9605.
2. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987; p 185. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986. Curran, D. P. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 715.
3. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987; p 185. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986. Curran, D. P. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 715.
4. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987; p 185. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986. Curran, D. P. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 715.
5. Keck, G. E.; Yates, J. B. J. Am. Chem. Soc., 1982, 104, 5829.
6. The allylsulfonation of alkenes with allylsulfone via the radical process were already reported. Harvey, I. W.; Phillips, E. D.; Whitham, G. H. J. Chem. Soc., Chem. Commun., 1990, 481. Chuang, C.-P. Synlett, 1990, 527.
7. The allylsulfonation of alkenes with allylsulfone via the radical process were already reported. Harvey, I. W.; Phillips, E. D.; Whitham, G. H. J. Chem. Soc., Chem. Commun., 1990, 481. Chuang, C.-P. Synlett, 1990, 527.
8. Allylstannanes 2e and 2f were prepared according to the reported procedure. Baldwin, J. E.; Adlington, R. M.; Birch, D. J.; Crawford, J. A.; Sweeney, J. B. J. Chem. Soc., Chem. Commun., 1986, 1339. Baldwin, J. E.; Adlington, R. M.; Lowe, C.; O'Neil, I. A.; Sanders, G. L.; Schofield, C. J.; Sweeney, J. B. J. Chem. Soc., Chem. Commun., 1988, 1030.
9. Allylstannanes 2e and 2f were prepared according to the reported procedure. Baldwin, J. E.; Adlington, R. M.; Birch, D. J.; Crawford, J. A.; Sweeney, J. B. J. Chem. Soc., Chem. Commun., 1986, 1339. Baldwin, J. E.; Adlington, R. M.; Lowe, C.; O'Neil, I. A.; Sanders, G. L.; Schofield, C. J.; Sweeney, J. B. J. Chem. Soc., Chem. Commun., 1988, 1030.
10. 4Sn: C, 53.07; H, 8.48%. Found: C, 53.01; H, 8.50%.
11. 1=COOMe), reacts with methyl acrylate 12 and 4 times faster than 1-butene and ethyl vinyl ether, respectively. This observation suggests that ester-substituted radicals are nucleophilic rather than electrophilic. Beranek, I.; Fischer, H. Free Radicals in Synthesis and Biology, Minisci, F., Ed.; Kluwer: Dordrecht, 1989; p 303.
12. Goswami, R. J. Org. Chem., 1985, 50, 5907.