Synthesis of 3-chloro-4-(dichloromethyl)-5-hydroxy-2 (5 H)-furanone, a potent mutagen

AA Padmapriya, G Just…

Index: Padmapriya, Abeysinghe A.; Just, George; Lewis, Norman G. Canadian Journal of Chemistry, 1985 , vol. 63, p. 828 - 832

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Citation Number: 94

Abstract

Starting from tetrachloroacetone 1 and (carbomethoxymethylene) triphenylphosphorane 4, the title compound 16 was prepared in five steps in 44% yield. Spectroscopic and chromatographic data indicated that this material was identical to a potent mutagen isolated from kraft pulp chlorination effluent. Various mutant Salmonella typhimurium strains (TA 98, 100, and 1537) behaved similarly when incubated with either 16 or the isolated mutagen.