P. E. Verkade, K. D. Vries, B. M. Wepster
Sep 2, 2010
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
The reaction of trans-1-chloro-2-butene with solutions of lithium, sodium, or potassium in liquid ammonia yields mainly trans-2-butene, 2,6-octadiene, and 3-methyl-1,5-heptadiene. Under the same conditions 3-chloro-1-butene yields mainly trans- and cis-2-butene (in a ratio of about 2 : 1), 3-methyl-1,5-heptadiene, and 3,4-dimethyl-1,5-hexadiene. The composition of the “bibutenyls” provides strong evidence that these products are formed in an SN2 reaction between carbanion and chloride.