Synthesis of isomerically pure. alpha.,. beta.-unsaturated nitriles via hydroalumination of alkynes

G Zweifel, JT Snow, CC Whitney

Index: Zweifel,G. et al. Journal of the American Chemical Society, 1968 , vol. 90, # 25 p. 7139 - 7141

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Citation Number: 36

Abstract

Vinylalanates derived from the hydroalumination of disubstituted alkynes with diisobutylaluminum hydride followed by treatment of the intermediate vinylalanes with methyllithium also react readily with cyanogen to give trans-a, p-unsaturated nitriles. Thus, 3- hexyne is converted by this procedure to trans-2-ethylpent-2-enenitrile.