Improved method for the reduction of unsaturated functional groups on solid supports

ORGN 907

Neil Brown, brownne@umkc.edu and Keith R. Buszek, buszekk@umkc.edu. Department of Chemistry, University of Missouri - Kansas City, Spencer Chemical Laboratories, 205 SCB, 5100 Rockhill Road, Kansas City, MO 64110-2481
A mild and improved method for reducing multiple bonds on various resins with diimide is described. The simple procedure readily generates diimide from 2-nitrobenzenesulfonohydrazide and triethylamine at room temperature. A number of representative multiple bonds in various steric and electronic environments were examined, including polar double bonds such as carbonyl and azo, for ease and selectivity of reduction. A general trend of reactivity was identified which revealed, inter alia, that terminal olefins, 1,2-disubstituted olefins, electron poor olefins, and terminal alkynes were the most easily reduced.