The cycloaddition of diazoalkanes to CS double bonds furnishes 1,3,4‐thiadiazolines which give rise to thiocarbonyl ylides and N2 in a cycloreversion. Thiocarbonyl ylides are nucleophilic 1,3‐dipoles which are interceptible by thiones or electron‐deficient alkenes and alkynes as dipolarophiles affording 1,3‐dithiolanes, dihydrothiophenes and thiolanes, respectively. In the absence of reaction partners, thiocarbonyl ylides undergo electrocyclization, dimerization, β‐H abstraction or Wagner‐Meerwein rearrangement.
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Huisgen et al. (1984) studied this question.
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