Cyclisation of Ortho -Cyclohexenyl Phenols via Epoxidation # |
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Authors: | K. C. Majumdar P. Chatterjee A. K. Kundu |
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Affiliation: | Department of Chemistry , University of Kalyani , Kalyani, 741235, W.B., INDIA |
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Abstract: | A number of ortho -cyclohexenyl phenols 2(a–i) have been cyclised by treatment with one equivalent of m-chloroper-oxybenzoic acid in refluxing benzene for 4 h to furnish linearly fused 1-hydroxy-1,2,3,4,4a,9a-hexahydrodibenzofurans 3(a–i) (70–80%) and bicyclic 3-hydroxy-1,3-ethanochromans 4(a–f) (10–20%). Products 3(a–i) were oxidised with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (excess) in refluxing dry xylene for 6 h to give 2,3-dihydrodibenzofuran-1 (2H)-ones 6(a–i) (85–95%). |
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