The synthesis and selected chemistry of 6-alkyl-6-carbalkoxy-and 6-alkyl-6-(aminocarbonyl)-2, 4-cyclohexadien-1-ones and cyclohexadienone ketals

…, FP Lavieri, C Salowey, P Sundararaman…

Index: Schultz, Arthur G.; Dittami, James P.; Lavieri, Frank P.; Salowey, Christina; Sundararaman, Padmanabhan; Szymula, Mary Beth Journal of Organic Chemistry, 1984 , vol. 49, # 23 p. 4429 - 4440

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Citation Number: 48

Abstract

The preparation of several 6-alkyl-6-carbalkoxy-2, 4-cyclohexadien-l-ones and corresponding C (1) ketals is described. Birch reduction-alkylation of methyl 2- methoxybenzoates gives 6-alkyl-6-carbomethoxy-1-meth-oxy-l, 4cyclohexadienea 4a-e and 5a4, and these are converted to bromo ketals 12 and 13, respectively, by treatment with N- bromoacetamide in methanol. Base-catalyzed dehydrobrominations of the bromo ketals ...