[reaction: see text] Treatment of diphenyl disulfide and terminal alkynes with gallium trichloride afforded (E)-1,2-diphenylthio-1-alkenes selectively (E/Z > 20/1). Alkenes also underwent this reaction to form trans adducts.

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Treatment of terminal acetylenes with butyllithium, followed by an addition of gallium trichloride, afforded the corresponding alkynylgallium reagents. The reaction of the resulting alkynylgallium with α-halo carbonyl compounds in the presence of triethylborane as a radical initiator provided β,γ-acetylenic carbonyl compounds in good yields.

Treatment of benzyl bromoacetate with 3-butenylgallium dichloride in ether in the presence of a catalytic amount of Et3B as a radical initiator provided benzyl 3-cyclopropylpropanoate in 64% yield via a radical addition–substitution sequence. The use of 3-butenylindium dichloride in place of the gallium reagent also afforded the same product in good yield.