Abstract
Treatment of tosylhydrazones of benzoin, benzoin acetate, and benzoin benzoate with alkali under protic and aprotic conditions yielded diphenyl acetylene together with desoxybenzoin. An increase in leaving aptitude of the adjacent group enhanced the formation of diphenyl acetylene. By treatment with LiAlH4 and with NaBH4, the tosylhydrazones gave stilbenes in good yields. Selective formation of cis- or trans-stilbene was observed in some cases. Key words: tosylhydrazone, benzoin derivatives, decomposition, metal complex hydrides.
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