Lewis acid mediated nucleophilic substitution reactions of 2-alkoxy-3, 4-dihydro-2H-1-benzopyrans: regiochemistry and utility in the synthesis of 3, 4-dihydro-2H-1- …

N Cohen, B Schaer, G Saucy, R Borer…

Index: Cohen, Noal; Schaer, Beatrice; Saucy, Gabriel; Borer, Rene; Todaro, Louis; Chiu, Anne-Marie Journal of Organic Chemistry, 1989 , vol. 54, # 14 p. 3282 - 3292

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Citation Number: 40

Abstract

The Lewis acid mediated nucleophilic substitution reactions of a variety of 2-alkoxy-, 2- hydroxy-, and 2-(acyloxy)-3, 4-dihydro-2H-l-benzopyrans (chromans) have been studied within the context of developing new synthetic routes to chroman-2-carboxylic acids, certain of which have utility as antioxidants and drug intermediates. The scope and limitations of these transformations have been determined. Treatment of 2-methoxychromans in the a- ...