REACTION OF PHENYLLITHIUM WITH 1-HALO-2-BUTENES

Phenyllithium reacted with cis- and trans-1-chloro-2-butene and trans-1-bromo-2-butene and gave a mixture of 3-phenyl-1-butene, cis- and trans-l-phenyl-2-butene, and cis- and trans-1-methyl-2-phenylcyclopropane. The ratio of the isomeric cyclopropanes was similar to that obtained from the addition of phenyllithium to 3-methylcyclopropene and confirmed the formation of this compound in the reaction. Phenylsodium and phenylmagnesium bromide in their reactions with the l-halo-2-butenes gave only the three olefins. © 1969, American Chemical Society. All rights reserved.