Cyclopropene Derivatives. IV. The Reactions of Acylcyclopropene

Abstract

Abstract The reactions of acylcyclopropenes, such as 3-benzoyl-1,2-diphenyl- and 3-acetyl-1,2-diphenyl-cyclopropene, were investigated. These ketones gave normal hydrazones with 2,4-dinitrophenylhydrazine. With p-toluenesulfonylhydrazine, the acetyl compound gave ordinary hydrazone, but the benzoyl derivative did not give its hydrazone. The reaction with hydrazine hydrate caused the expansion of the cyclopropene ring and produced pyridazine derivatives in both the ketones. The carbenic decomposition of 3-acetyl-1,2-diphenylcyclopropene p-toluenesulfonylhydrazone with sodium methoxide in diglyme gave diphenylacetylene and 3,4-diphenyl-6-methylpyridazine. On irradiation with ultraviolet light, 3-benzoyl-1,2-diphenylcyclopropene produced 1,2,4,5-tetraphenylbenzene. In the case of 3-acetyl-1,2-diphenylcyclopropene, the same benzene derivative and 1,2,4,5-tetraphenyl-3,6-diacetyltricyclo[3,1,0,02,4]hexane were obtained. The latter material was transformed into a benzene derivative upon further irradiation. Tricyclohexane could be an intermediate in the transformation of ketones to a benzene derivative.