Journal of the American Chemical Society

Selective hydroboration of conjugated diynes with dialkylboranes. A convenient route to conjugated cis-enynes,. alpha.,. beta.-acetylenic ketones, and cis, cis-dienes

G Zweifel, NL Polston

Index: Zweifel,G.; Polston,N.L. Journal of the American Chemical Society, 1970 , vol. 92, p. 4068 - 4071

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Citation Number: 116

Abstract

Abstract: The monohydroborations of dodeca-S, 7-diyne, 2, 7-dimethylocta-3, S-diyne, and 2, 2, 7, 7-tetramethylocta-3, s-diyne with disiamylborane [bis (3-methyl-2-butyl) borane] proceed to place the boron preferentially at the internal positions of the diyne system. The organoboron intermediates upon protonolysis with acetic acid give the corresponding cis- enynes in high yields. Oxidation of the monohydroboration products with alkaline ...

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