The Journal of Organic Chemistry

A highly stereoselective synthesis of vinyl bromides and chlorides via disubstituted vinylsilanes

RB Miller, G McGarvey

文献索引：Miller,R.B.; McGarvey,G. Journal of Organic Chemistry, 1978 , vol. 43, p. 4424 - 4431

被引用次数: 149

摘要

A detailed study of the utility of vinylsilanes as intermediates in a stereoselective synthesis of vinyl halides is described. The requisite vinylsilanes are readily available from alkynes by hydroalumination-protonolysis or hydrosilation. Various methods of desilicohalogenation of intermediate dihalides from vinylsilanes 2a and 3a are compared. The effect of the alkyl substituent on the vinylsilane upon yield and stereoselectivity of the overall halogena-tion- ...

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