Thiocarbonyl Ylides. Attempted Preparation and Related Reactions

S Mitamura, M Takaku, H Nozaki

Index: Mitamura,S. et al. Bulletin of the Chemical Society of Japan, 1974 , vol. 47, p. 3152 - 3157

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Citation Number: 9

Abstract

The attempted preparation of thiocarbonyl ylides (I) by the proton abstraction of thiouronium salts (III) has disclosed a fast isomerization of I to enethiols (V)(Y= H) and an alternative desulfurization to enediamines (VII)(Y= Ph), the by-products being olefins (VIII) and sulfides (IX). The second route to I examined consists of the reaction of tetramethylthiourea (II) with diazomalonate, which gives rise to enediamine (VII g). Rotation about the C= C bond of ...