The Journal of Organic Chemistry

Chlorination studies of unsaturated materials in nonpolar media. VIII. Ionic chlorination of some simple allenes

ML Poutsma

Index: Poutsma,M.L. Journal of Organic Chemistry, 1968 , vol. 33, p. 4080 - 4084

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Citation Number: 24

Abstract

Chlorinations of tetramethylallene (3), 1, l-dimethylallene (8), and allene have been carried out in nonpolar media in the presence of oxgen as a radical inhibitor. The only chlorination product of 3 at 25" in C2FsC18 solution is 3-chloro-2, 4-dimethyl-l, 3-pentadiene (4). However, the hydrogen chloride coproduct leads to extensive isomerization of 3 to form 2, 4- dimethyl-l13-pentadiene(5) and subsequent telomerization of 5 in large part to 1, 3, 3, 5, E ...

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