title: Formation mechanism of furfuryl sulfides from o-furfuryl dithiocarbonates: density functional theory study for aromatic [3,3]-sigmatropic rearrangement.
abstract: 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.
authors.affiliation: Liberal Arts Education Center, Aso Campus, Tokai University, 5435 Kawayo, Minami-Aso, Kumamoto, Japan.
authors.forename: Masashi
authors.initials: M
authors.lastname: Eto
authors.forename: Koki
authors.initials: K
authors.lastname: Yamaguchi
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Yoshitake
authors.forename: Kazunobu
authors.initials: K
authors.lastname: Harano
mesh_terms: D000838:Anions / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013440:Sulfides / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D000838:Anions; D002254:Carbonates; D005663:Furans; D013440:Sulfides