The Journal of Organic Chemistry

Photochemical and acid-catalyzed dienone-phenol rearrangements. The effect of substituents on the regioselectivity of 1, 4-sigmatropic rearrangements of the type A …

AG Schultz, SA Hardinger

Index: Schultz, Arthur G.; Hardinger, Steven A. Journal of Organic Chemistry, 1991 , vol. 56, # 3 p. 1105 - 1111

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Citation Number: 26

Abstract

Birch reduction of isophthalic acid and 3-cyanobenzoic acid followed by (1) methylation of the resulting enolate with methyl iodide and (2) esterification with diazomethane provided 2- carbomethoxy-and 2-cyan0-6-methyl-6-carbomethoxy-1, 4-cyclohexadiene 9 and 25. Type A photorearrangements of a series of 2-carbomethoxy-, 2-cyano-, 2-methoxy-, and 2-methyl- 4-carbomethoxy-4-methyl-2, 5-cyclohexadien-l-ones 11, 26, 45a, and 45b gave 4- ...