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

Eto M,Yamaguchi K,Yoshitake Y,Harano K

doi

10.1248/cpb.59.681

subject

Has Abstract

pub_date

2011-01-01 00:00:00

pages

681-5

issue

6

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/59.681

journal_volume

59

pub_type

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