Reaction of propargylic substrates with organocopper species. Synthetic aspects

TL Macdonald, DR Reagan…

Index: Macdonald, Timothy L.; Reagan, David R. Journal of Organic Chemistry, 1980 , vol. 45, # 23 p. 4740 - 4747

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Citation Number: 63

Abstract

The reaction of propargylic substrates with organocopper species can yield two major products, a substituted allene or a new acetylene. This paper is a study of the factors which influence the distribution of these products in this displacement (eg, 1-2+ 3). Those factors are (1) organocopper reagent stochiometry (R3CuLiz, RzCu-, RCu metal salt),(2) organocopper species concomitant salt or counterion (It@', Li'),(3) acetylenic site ...