A novel cyclization reaction of alkylthiodiphenylcyclopropenium ions with acyclic 1, 3-diketones to give cyclopentadienols.

H Yoshida, M Nakajima, T Ogata, K Matsumoto…

Index: Yoshida, Hiroshi; Nakajima, Mikito; Ogata, Tsuyoshi; Matsumoto, Kiyoshi; Acheson, R. Morrin; Wallis, John D. Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 10 p. 3015 - 3019

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Citation Number: 13

Abstract

Reaction of methylthio-, ethylthio-, and benzylthiodiphenylcyclopropenium salts with 2, 4- pentanedione (3a) and ethyl acetoacetate (3b) yielded the cyclopentadienol derivatives (4) by ring expansion. One of the products 4a was shown to be 4-acetyl-5-hydroxy-5-methyl-1- methylthio-2, 3-diphenyl-1, 3-cyclopentadiene by X-ray crystallography. Chemical transformation of the products yielded some cyclopentenones. Triphenylcyclopropenium ...