Synthesis and reactions of 2-lithio-3-chlorobicyclo [2.2. 1] hept-2-ene. Generation of the trimer of bicyclo [2.2. 1] hept-2-yne

PG Gassman, I Gennick

Index: Gassman,P.G.; Gennick,I. Journal of the American Chemical Society, 1980 , vol. 102, p. 6863

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Citation Number: 59

Abstract

1 2 loss of lithium chloride under the reaction conditions (large excess of organolithium) then produced bicyclo [2.2. I] hept-2-yne (3) as a highly reactive intermediate which immediately added the excess n-butyllithium. As part of a program designed to explore the chemistry of highly strained acetylenes, we desired to generate 3 in the absence of excess organolithiums. We now report on the synthesis and reactions of 2, including its ...