PHOTOREDUCTION OF CARBONYL COMPOUNDS BY TRIBUTYL TIN HYDRIDE

Article abstract of DOI:10.1016/S0040-4020(01)91174-3

The photochemical reactions of cyclohexanone, acetone, 1-naphthaldehyde, 2-naphthaldehyde and 2-acetonaphthone with tributyltin hydride are chain processes leading to the tributyltin ethers of the derived alcohols as the major products, and the analogous ethers of the corresponding pinacols as the most abundant minor products, rather than simple reductions to the alcohols themselves as previously reported.Chain termination for the reductions of those compounds that have a n,?^* triplet state occurs primarily by coupling of tributyltin radicals to form hexabutylditin, but by coupling of the ketyl radicals to form pinacol ethers for those compounds that have a ?,?^* triplet state.Ring reduction is an important process for the aromatic compounds with ?,?^* triplet states that were studied.Analysis were performed using (1)H, (13)C and (119)Sn NMR.