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

• Eto Masashi

  Liberal Arts Education Center, Aso Campus, Tokai University

• Yamaguchi Koki

  Faculty of Pharmaceutical Sciences, Sojo University

• Yoshitake Yasuyuki

  Faculty of Pharmaceutical Sciences, Sojo University

• Harano Kazunobu

  Faculty of Pharmaceutical Sciences, Sojo University

Bibliographic Information

Other 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.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 59 (6), 681-685, 2011

  The Pharmaceutical Society of Japan

Keywords

• furfuryl alkyl sulfide
• dithiocarbonate
• thione-to-thiol rearrangement
• aromatic [3,3]-sigmatropic rearrangement
• density functional theory calculation

Details

• CRID: 1390001204173695232
• NII Article ID: 130000747989
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.59.681
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 11094929
• Web Site: http://id.ndl.go.jp/bib/11094929
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I11094929
• Web Site: http://www.jstage.jst.go.jp/article/cpb/59/6/59_6_681/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed