The chemistry of cycloheptatriene: Part II: Reduction of cycloheptatriene to cycloheptadiene and cycloheptene

Abstract

Abstract Reduction of cycloheptatriene (I) and cycloheptadiene (II) with 2 equivalents of sodium in liquid ammonia yields ‐ after addition of ethanol ‐ cycloheptadiene and cycloheptene (III), respectively. These reactions proceed via coloured intermediates. Reduction of I with 4 equivalents of sodium gives only III. Carbonation of the reaction mixture of I and 2 equivalents of sodium yields a cycloheptadiene monocarboxylic acid whereas no carboxylic acid has formed upon carbonation of the reaction mixture of II and 2 equivalents of sodium.