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Density functional theory (DFT) calculations at the B3LYP/6-31G(d) and B3LYP/6-31G+(d) levels demonstrated that O-furfuryl S-alkyl dithiocarbonate (1) undergoes aromatic [3,3]-sigmatropic rearrangement to the energetically unfavorable S-(2-methylene-2,3-dihydrofuran-3-yl) S-alkyl dithiocarbonate (2'), which then rearranges to furfuryl alkyl sulfide (3) with COS extrusion to regain the aromaticity lost in the first step.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Formation Mechanism of Furfuryl Sulfides from O-Furfuryl Dithiocarbonates: Density Functional Theory Study for Aromatic [3,3]-Sigmatropic Rearrangement