Double prototropic rearrangement of cis-1-chlorohex-2-en-4-yne by phenyl-lithium
Abstract
Chlorination–rearrangement of hex-1-en-4-yn-3-ol gave 1-chlorohex-2-en-4-yne, which was separated into the cis- and trans-isomers. Phenyl-lithium and allyl chloride yielded allylbenzene, but the coupling reaction of the cis-isomer with phenyl-lithium at 0° was followed by a double prototropic rearrangement, affording a mixture of cis- and trans-1-phenylhex-3-en-5-yne.