Decomposition of tosylhydrazones of benzoin, benzoin acetate, and benzoin benzoate with alkali and metal complex hydrides

Article abstract of DOI:10.1139/v96-025

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.