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

1961; Royal Netherlands Chemical Society; Volume: 80; Issue: 11 Linguagem: Inglês

10.1002/recl.19610801109

1878-7096

A. P. ter Borg, A. F. Bickel,

Asymmetric Synthesis and Catalysis

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.