The reaction of hydrogallium(III) dichloride (HGaCl2) with olefines, acetylenes, and α,β-unsaturated ketones

Article abstract of DOI:10.1016/0022-328X(93)80319-7

The reaction of HGaCl2 with 1-octene yields 1-octylgallium(III) dichloride in 77percent yield, but with 2-octene a 2:1 mixture of 2- and 3-octylgallium dichloride(III) is obtained in 88percent yield, and the reaction of (E)-stilbene gives an even more complex mixture.Hydrogallation of 1,4-diphenylbutadiene with HGaCl2 followed by hydrolysis yields 1,4-diphenylbutane in 53percent yield.The reactions of diphenylacetylene and 4-octyne under the same conditions give (E)-stilbene and (E)-4-octene in 76percent and 63percent yield, respectively, while 1-octyne undergoes polymerization. 2-Benzoylstyrene (calcone) reacts with HGaCl2 to give, as the main product, a compound arising from 1,4-addition of the H-Ga bond across the enone system, together with a double hydrogallation product.