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 (VIIg). Rotation about the C=C bond of enediamines is discussed on the basis of IR and NMR spectra.
Die Kondensation der Ketone (I) mit den Bromiden (II) in Benzol in Gegenwart von Triäthylamin liefert die Sulfide (III) (54‐70% Ausbeute), die zu den Dihydrothiophenen (IV) (40‐ 100%) cyclisiert werden.
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