Highly Regiocontrolled and Efficient Synthesis of Vinyl- And Allylstannanes via Lewis Acids Pd-Catalyzed Hydrostannation of Allenes: Scope and Limitations

Journal of Organic Chemistry

Volumn 62, Issue 9, 1997, Pages 2963-2967

  Gevorgyan, Vladimir ^a   Liu, Jian Xiu ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001565674     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9624049     Document Type: Article

References (29)

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17. The germanium analogue of 7 was reported to be synthesized and fully characterized. Bochkarev, M. N.; Maiorova, L. P.; Skobeleva, S. E.; Razuvaev, G. A. Izv. Akad. Nauk. SSSR, Ser. Khim. 1979, 1854. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Eng. Transl.) 1979, 1717.
18. The germanium analogue of 7 was reported to be synthesized and fully characterized. Bochkarev, M. N.; Maiorova, L. P.; Skobeleva, S. E.; Razuvaev, G. A. Izv. Akad. Nauk. SSSR, Ser. Khim. 1979, 1854. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Eng. Transl.) 1979, 1717.
19. For the syntheses and properties of palladium hydrides, see a recent excellent review: Grushin, V. Chem. Rev. 1996, 96, 2011 and references therein.
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21. 4 used. (a) Gevorgyan, V. N.; Ignatovich, L. M.; Lukevics, E. J. Organomet. Chem. 1985, 284, C31.
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23. 16 and, thus, not reliable.
24. Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468.
25. The irradiation at either one of the olefinic protons of 15 did not display any NOE at another oleflnic portion. In contrast, the irradiation of methylene protons at the γ-position of 15 exhibited significant NOE at both olefinic protons.
26. 16 and thus is not reliable to distinguish the structures 10 and 15 by this means.
27. 3 carbon in allylstannanes. This is in a contrast to the low field chemical shift of allylbenzenes (ca. 40 ppm).
28. Tanaka, H.; Abdul Hai, A. K. M.; Ogawa, H.; Torii, S. Synlett 1993, 835.
29. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1981.