Butyllithium-induced dimerization of pent-3-en-1-yne and related additions

Article abstract of DOI:10.1016/0022-328X(91)86132-A

The enynes HC<*>CCH=CHCH2R (R = H, Me, OMe, NMe2, SMe), are converted into dimers by treatment with slightly more than two equivalents of butyllithium.The Z-configuration predominates in the dimers obtained after aqueous work-up.The lithiated enynes (R = H, Me, SMe) and acetylenic compounds LiC<*>CCH2R (R = SMe, C6H5) add in an analogous way to the double bond of LiC<*>CCH=CH2.