Reaction of dialkylthioketenes with tetracyanoethylene oxide yields dicyanomethylenethiiranes in a sequence involving [3 + 2] cycloaddition, cycloreversion and rearrangement. In contrast, a thioketene with a sulfide moiety reacts preferentially on the latter to give the stable sulfur ylide 9.
G. Adiwidjaja, O. Bolte, B. Dietz and E. Schaumann, J. Chem. Soc., Perkin Trans. 1, 1993, 2385 DOI: 10.1039/P19930002385
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