Synthesis of diols using the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate)


Celik M., Alp C., Coskun B., Gultekin M. S. , Balci M.

TETRAHEDRON LETTERS, vol.47, no.22, pp.3659-3663, 2006 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 47 Issue: 22
  • Publication Date: 2006
  • Doi Number: 10.1016/j.tetlet.2006.03.137
  • Journal Name: TETRAHEDRON LETTERS
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.3659-3663
  • Keywords: phenyliodine(III) bis(trifluoroacetate), PIFA, oxidation, rearrangement, 1.2-diols, 1.3-diols, HIGH-TEMPERATURE BROMINATION, CIS, BENZONORBORNADIENE

Abstract

1.2- and 1.3-Bis(trifluoroacetoxy) alcohols are easily obtained from the one-pot reaction of alkenes with phenyliodine(III) bis(trifluoroacetate) (PIFA) in the absence of any additive or catalyst. The products were converted into the corresponding diols by ammonolysis. The use of bicyclic alkenes has shown that rearranged 1,3-diacetoxy alcohols are mostly formed as the major products. (c) 2006 Elsevier Ltd. All rights reserved.