The Journal of Organic Chemistry

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

RB Miller, G McGarvey

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

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Citation Number: 149

Abstract

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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