A novel oxidative cleavage reaction with Pb(OAc)4 via dithioacetal derivatives.

• HIROI KUNIO

• SATO SHUKO

• MATSUO KAZUHIDE

Abstract

The oxidative cleavage of 2-alkyl-2-(1-hydroxyalkyl)-1, 3-dithianes (1-5) and 2-(1-hydroxyethyl)-2-methyl-1, 3-dithiolane (11) with Pb (OAc)₄ gave 3-alkyl-1, 4-dithiepan-2-ones (7a-e) and 1, 4-dithian-2-one (12), respectively, in fairly good yields. Analogously, the treatment of 2-alkylidene-1, 3-dithianes (13a-e) with Pb (OAc)₄ resulted in a ring expansion to give 7a-e, whereas the reaction of 2-benzylidene-1, 3-dithiane (13f) with Pb (OAc)₄ did not produce the expected ring expansion product, instead giving 2-(α-acetoxybenzylidene)-1, 3-dithiane (8).

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 28 (2), 558-566, 1980

  The Pharmaceutical Society of Japan

Keywords

• Pb (OAc)<SUB>4</SUB>

Details

• CRID: 1390001204165682048
• NII Article ID: 110003623941
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.28.558
• COI: 1:CAS:528:DyaL3cXltFCns70%3D
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/28/2/28_2_558/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1981017390
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed