Tetrahedron

Synthesis of α, β-unsaturated γ-lactones via photooxygenation of 2, 3-dihydrofurans followed by ferrous ion-catalyzed gem-dehydration

YZ Chen, LZ Wu, ML Peng, D Zhang, LP Zhang…

Index: Chen, Yu-Zhe; Wu, Li-Zhu; Peng, Ming-Li; Zhang, Dong; Zhang, Li-Ping; Tung, Chen-Ho Tetrahedron, 2006 , vol. 62, # 46 p. 10688 - 10693

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Citation Number: 17

Abstract

Several alkyl and aryl substituted 2, 3-dihydrofurans 1a–1e were synthesized and their reactions with singlet oxygen were investigated. Photooxygenation of 1a–1e in carbon tetrachloride at ambient temperature exclusively yields allylic hydroperoxides 4a–4e. Treatment of these hydroperoxides with aqueous ferrous sulfate solution affords the corresponding α, β-unsaturated γ-lactones 6a–6e with high yields. This work provides an ...

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