Fig. 8: Proposed mechanism of the herein presented alkylidene-homocoupling reaction.
From: Synthesis of highly substituted alkenes by sulfur-mediated olefination of N-tosylhydrazones
Path A (red arrow) entails a Barton-Kellogg reaction and path B (blue arrow) a direct thiirane formation from carbene and thioketone. The desulfurization is mainly mediated by a polysulfide chain, while eliminated p-toluenesulfinate can also enable product formation (dashed reaction sequence). The colored spheres represent aryl moieties.
