Journal of the American Chemical Society

Stereochemistry of addition reactions of allenes. III. Free-radical reactions of 2, 3-pentadiene and 2-pentyne with tert-butyl hypochlorite

LR Byrd, MC Caserio

Index: Byrd,L.R.; Caserio,M.C. Journal of the American Chemical Society, 1970 , vol. 92, p. 5422 - 5431

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Citation Number: 16

Abstract

Abstract: Free-radical chlorination of 2, 3-pentadiene with t-butyl hypochlorite has been found to give substitution products that may be formally considered as arising from both allylic and allenic hydrogen abstraction. Allenic abstraction led to formation of 4-chloro-2- pentyne which was also formed in the related chlorination of 2-pentyne. No 2-chloro-2, 3- pentadiene was detected in the products from either hydrocarbon. Also, optically active 2, ...