Manganese(III) acetate-mediated oxidative cyclization of a-methylstyrene and trans-stilbene with b-ketosulfones

Molecules. 2013 Apr 11;18(4):4293-307. doi: 10.3390/molecules18044293.

Abstract

A convenient microwave irradiation protocol was utilized for the synthesis of b-ketosulfones 1-5 in good yields. These sulfones reacted with alkenes through a radical oxidative cyclization mediated by Mn(OAc)3. Dihydrofurans 6-10 were obtained in moderate to good yields starting from 1,1-disubstituted alkenes. Dihydrofurans 11-15 were synthesized in moderate yields and unexpected cyclopropanes 16-19 were obtained in low yields starting from 1,2-disubstituted alkenes. This protocol offers access to various dihydrofurans which could be tested for their antiparasitic potential.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry*
  • Alkenes / chemistry
  • Antiparasitic Agents / chemical synthesis
  • Antiparasitic Agents / chemistry
  • Cyclization
  • Cyclopropanes / chemical synthesis
  • Furans / chemical synthesis
  • Furans / chemistry
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction*
  • Stilbenes / chemistry
  • Styrenes / chemistry*
  • X-Rays

Substances

  • Acetates
  • Alkenes
  • Antiparasitic Agents
  • Cyclopropanes
  • Furans
  • Organometallic Compounds
  • Stilbenes
  • Styrenes
  • manganese(III) acetate dihydrate
  • vinyltoluene