Hexachloroacetone/triphenylphosphine: a mild reagent for the regioselective and stereospecific production of allylic chlorides from the alcohols

RM Magid, OS Fruchey, WL Johnson…

Index: Magid,R.M. et al. Journal of Organic Chemistry, 1979 , vol. 44, # 3 p. 359 - 363

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Citation Number: 83

Abstract

Allylic alcohols 1-16 react with hexachloroacetone/triphenylphosphine in less than 20 min at 10-15" C to produce excellent yields of the corresponding chlorides. Isolation is accomplished simply by flash distillation. The conversion occurs with total preservation of double bond geometry and with> 99% inversion of configuration for optically active alcohol 8. All of the primary and secondary alcohols give predominantly the unrearranged ...