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, cilt.47, sa.22, ss.3659-3663, 2006 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 47 Sayı: 22
  • Basım Tarihi: 2006
  • Doi Numarası: 10.1016/j.tetlet.2006.03.137
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3659-3663
  • Anahtar Kelimeler: phenyliodine(III) bis(trifluoroacetate), PIFA, oxidation, rearrangement, 1.2-diols, 1.3-diols, HIGH-TEMPERATURE BROMINATION, CIS, BENZONORBORNADIENE
  • Atatürk Üniversitesi Adresli: Evet

Özet

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.