ALIPHATIC THIOETHERS BY S-ALKYLATION OF THIOLS VIA TRIALKYL BORATES


Güneş D. , Sirkecioğlu O. , BICAK N.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.185, no.8, pp.1685-1690, 2010 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 185 Issue: 8
  • Publication Date: 2010
  • Doi Number: 10.1080/10426500903213563
  • Title of Journal : PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Page Numbers: pp.1685-1690

Abstract

A simple and convenient one-pot procedure is described for the synthesis of thioethers via boron esters. This procedure involves in-situ generation of alkyl sulfates by reaction of trialkyl borates with concentrated sulfuric acid and subsequent reaction with thiols in the presence of pyridine. The reactions with boron esters of primary or secondary alcohols proceed cleanly at 100 degrees C and afford aliphatic thioethers in reasonable yields (59-93%) within 24 h. Interestingly, the 1H NMR spectra of the products showed no sign of positional isomerisms. The method fails however with thiophenol and does not yield aromatic thioethers, due to electrophilic substitution at the phenyl ring.