Novel dienone-phenol type rearrangement of 4,4-disubstituted cyclohexadienone system using thiosilane

Chem Commun (Camb). 2010 Feb 7;46(5):797-9. doi: 10.1039/b915294f. Epub 2009 Dec 9.

Abstract

Thiosilane and a catalytic amount of a Brønsted acid mediate the novel domino-type rearrangement reaction of the 4,4-disubstituted cyclohexadienones to produce the 3,4-disubstituted benzenethioethers; the key step is 1,2-addition of thiosilane to dienone.

MeSH terms

  • Acids / chemistry
  • Catalysis
  • Cyclohexenes / chemistry*
  • Ketones / chemistry
  • Molecular Structure
  • Silanes / chemistry*
  • Sulfhydryl Compounds / chemical synthesis
  • Sulfhydryl Compounds / chemistry

Substances

  • Acids
  • Cyclohexenes
  • Ketones
  • Silanes
  • Sulfhydryl Compounds
  • cyclohexadienone