Oxidation reaction of 4-allyl-4-hydroperoxy-2-methoxycyclohexa-2,5-dienone in the presence of potassium permanganate without a co-oxidant

Mehmet Serdar Gültekin and Haydar Göksu

Department of Chemistry, Faculty of Sciences, Atatürk University, Erzurum, Türkiye

Kaynaşlı Vocational College, Düzce University, Düzce, Türkiye

Abstract: 4-Allyl-4-hydroperoxy-2-methoxycyclohexa-2,5-dienone (5) was synthesized by photooxygenation of commercially available Eugenol in the presence of tetraphenylporphyrin (TPP) as a singlet oxygen sensitizer. The brief and one-pot syntheses of some natural product skeletons were conducted using the corresponding allylic hydroperoxide at different temperatures (0 oC and room temperature) with potassium permanganate (KMnO 4) in mild condition at N 2(g) atm.

Keywords : Allylic hydroperoxide; singlet oxygen; photooxygenation; eugenol, natural product. © 2016 ACG Publications. All rights reserved.