Canadian Journal of Chemistry

ipso Nitration. XXIII. Reactions of cyclohexadiene adducts from nitration of 4-ethyltoluene in acetic anhydride

A Fischer, GN Henderson

Index: Fischer, Alfred; Henderson, George N. Canadian Journal of Chemistry, 1981 , vol. 59, p. 2314 - 2327

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Citation Number: 12

Abstract

The diastereoisomers of 4-ethyl-1-methyl-4-nitrocyclohexa-2, 5-dienyl acetate (1) and 1- ethyl-4-methyl-4-nitrocyclohexa-2, 5-dienyl acetate (2) are stereospecifically reduced to the corresponding nitrocyclohexadienols with aluminum hydride. Each dienol is stereospecifically methylated to the corresponding methyl ether with methyl iodide, silver oxide, and potassium hydroxide. Acid-catalysed solvolysis of the acetates 1 and 2 results ...