The Journal of Organic Chemistry

A regioselective decarbonylation

JL Belletire, ML Guerra

Index: Belletire, John L.; Guerra, Maria L. Journal of Organic Chemistry, 1992 , vol. 57, # 10 p. 2970 - 2972

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Abstract

Conclusion Photolytic bromination at benzylic positions by diethyl bromomalonate is a slow process probably indicative of short radical chain length. Despite this, it appears that the major chain-propagating species is the diethyl malonyl radical. This species shows sensitivity toward electronic changes which are typical of electrophilic radicals. Its size, however, causes it to be very selective with regard to reaction at hindered benzylic sites. ...