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.
J. C. Craig and R. J. Young, J. Chem. Soc. C, 1966, 578 DOI: 10.1039/J39660000578
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