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

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

Masashi Eto, Koki Yamaguchi, Yasuyuki Yoshitake, Kazunobu Harano

Chem Pharm Bull (Tokyo). 2011;59(6):681-5.

PMID: 21628900

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP13678676	Furfuryl sulfide		13678-67-6	Price

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