1,2-Dibromotetrachloroethane: An efficient reagent for many transformations by modified Appel reaction

Essiz S., DAŞTAN A.

Turkish Journal of Chemistry, vol.43, no.1, pp.150-156, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 43 Issue: 1
  • Publication Date: 2019
  • Doi Number: 10.3906/kim-1804-41
  • Journal Name: Turkish Journal of Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.150-156
  • Keywords: 1,2-dibromotetrachloroethane, Alkyl bromides, Appel reaction, Configuration inversion, Ring-opening reaction
  • Hakkari University Affiliated: No

Abstract

An efficient and facile method has been developed for the synthesis of alkyl bromides from various alcohols under mild conditions using a triphenylphosphine (PPh 3) /1,2-dibromotetrachloroethane (DBTCE) complex in excellent yields and very short time (5 min). This method can also be applied for the transformation of chiral alcohols to their corresponding bromides in very high enantiomeric excess. The PPh 3 /DBTCE complex is also successfully applied to ring-opening reactions of cyclic ethers in mild conditions. Esterification, amidation, and formation of acid anhydrides under very mild experimental conditions are also successfully accomplished by following a modification of the Appel reaction protocol in this work.