Organic reducing agents: some radical chain reactions of ketyl and 1, 3-dioxolanyl radicals with activated bromides

F Fontana, RJ Kolt, Y Huang…

Index: Fontana, Francesca; Kolt, Ralph J.; Huang, Youqin; Wayner, Danial D. M. Journal of Organic Chemistry, 1994 , vol. 59, # 16 p. 4671 - 4676

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Citation Number: 31

Abstract

The radical chain reduction of primary and secondary a-bromo esters by 2-propanol and 2- methyldioxolane has been shown to be a kinetically viable process with average chain lengths of> 10 at temperatures between 30 and 60" C. For electron-deficient bromides, these simple organic reagents may effectively replace the more commonly used (and more expensive) organosilicon or tin hydides. Some mechanistic insights have been obtained ...