Ceric ammonium nitrate oxidative-cleavage reaction of some lignin model compounds. Role of the benzylic hydroxyl group

TH Fisher, SM Dershem, TP Schultz

Index: Fisher, Thomas H.; Dershem, Stephen M.; Schultz, Tor P. Journal of Organic Chemistry, 1988 , vol. 53, # 7 p. 1504 - 1507

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Citation Number: 18

Abstract

A series of 0-1 lignin model compounds was synthesized and then oxidized with ceric ammonium nitrate (CAN) in aqueous acetonitrile. The compounds studied were 1, 2- diarylethanols with either a p-hydroxy (la-e) or a p-methoxy (2a-e) on the 1-ring and the following para substituenb on the 2-ring:(a) H,(b) C1,(c) Me,(d) OMe, and (e) NOP. Reactions of p-hydroxyl compounds la-e with CAN resulted in the formation of a red ...