The Journal of Organic Chemistry

Reactions of anthranilium salts with nucleophiles: adduct formation and rearrangement

RK Vander Meer, RA Olofson

Index: Vander Meer, Robert K.; Olofson, R. A. Journal of Organic Chemistry, 1984 , vol. 49, # 18 p. 3373 - 3377

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Citation Number: 8

Abstract

3-Unsubstituted anthranilium salts 1 react with alcohols in the presence of bases to yield adducts 5 which rearrange to the esters 4 when refluxed in xylene. Similar processes involving 1 and cyanide or azide also have been observed. Evidence favoring benzoazetinones 2 as rearrangement intermediates is presented. The chemistry of 1 with phosphines and phosphites also is described. For example, treatment of IC with trimethyl ...