The Base-Induced Pyrolysis of Tosylhydrazones of α, β-Unsaturated Aldehydes and Ketones. A Convenient Synthesis of Some Alkylcyclopropenes

GL Closs, LE Closs, WA Boll

Index: Closs,G.L. et al. Journal of the American Chemical Society, 1963 , vol. 85, p. 3796 - 3800

Full Text: HTML

Citation Number: 120

Abstract

Tosylhydrazones of a number of o, p-unsaturated aldehydes and ketones have been prepared. On reaction with sodium methoxide in aprotic media at 160-220" alkyl-substituted cyclopropenes are formed. The yields vary from excellent to poor depending mainly on the degree of p-substitution of the tosylhydrazone. The sequence: tosylhydrazone-F diazoalkene-t alkenylcarbene+ cyclopropene is proposed as the most suitable description ...