ChemInform Abstract: Regioselective Allylation and Alkylation of Electron‐Deficient Alkenes with Organogallium and Organoindium Reagents.

Abstract

reactions of organo-metal compounds reactions of organo-metal compounds O 0350 -070Regioselective Allylation and Alkylation of Electron-Deficient Alkenes with Organogallium and Organoindium Reagents.α,β-Unsaturated nitrile and/or carbonyl compounds react with triorganogallium or indium reagents to give the 1,4-addition products selectively. A similar methylation of the electron-deficient alkenes (Ia), (Ib) is achieved with trimethylgallium. On the other hand, allylgallium or allylindium sesquihalides, generated from allyl halide and gallium (or indium) metal, react with α,β unsaturated carbonyl compounds such as (IIb) to form a 1,2-adduct [cf. (XI)], whereas the nitrile (IIa) reacts in the 1,4-mode. -(ARAKI, SHUKI; HORIE,