Oxidations of alkenes with hypervalent iodine reagents: an alternative ozonolysis of phenyl substituted alkenes and allylic oxidation of unsubstituted cyclic alkenes

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Atmaca U., Usanmaz H. K., Çelik M.

TETRAHEDRON LETTERS, cilt.55, sa.14, ss.2230-2232, 2014 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 55 Sayı: 14
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1016/j.tetlet.2014.02.076
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2230-2232
  • Anahtar Kelimeler: Allylic hydroperoxide, Oxidative cleavage, Hypervalent iodine, Ozonolysis, Alkenes, ORGANIC-SYNTHESIS, CLEAVAGE
  • Atatürk Üniversitesi Adresli: Evet

Özet

Unsaturated C=C double bonds with a phenyl substituent can be cleaved with iodylbenzene and iodosylbenzene to give carbonyl compounds. It is believed that the reactions occur via a radical pathway. The allylic oxidation of cyclic alkenes lacking a phenyl substituent was achieved in acetonitrile/water mixture (3:1) also using iodylbenzene and iodosylbenzene. (C) 2014 Elsevier Ltd. All rights reserved.