CYCLOADDITIONS OF ACETYLENIC ORGANOTINS : SYNTHETIC APPLICATIONS OF POLYFUNCTIONAL CYCLIC VINYLTINS

Article abstract of DOI:10.1016/0040-4020(89)80023-7

A novel preparation of functional vinyltins is described.It involves the regiospecific <4+2> cycloaddition of functional alkynyltins with dienes such as 1,3-butadiene, 2,3-dimethyl-1,3-butadiene or 1-substituted 1,3-butadienes.These cyclic vinyltins, bearing an ester, ketone, amide or nitrile group are converted into carbonylated, halogenated or sulfurized compounds.After reduction of the ester or ketone group, transmetallation leads to functional 1,4-cyclohexadienyllithium which react easily with carbon dioxide, aldehydes or ketones to give substituted 1(3H)-4,7-dihydro-isobenzofuranones or 1,4-diols. ofuranones or 1,4-diols.