Synthesis of 1,2,4-trioxepanes and 1,2,4-trioxocanes via photooxygenation of homoallylic alcohols |
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Authors: | Singh Chandan Pandey Shilpi Saxena Gunjan Srivastava Nisha Sharma Malvika |
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Institution: | Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow-226001, India. chandancdri@yahoo.com |
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Abstract: | Homoallylic alcohols 4a-d, easily accessible in two steps from cyclopropyl methyl ketone, underwent a highly regioselective reaction with singlet oxygen to yield gamma-hydroxyhydroperoxides 5a-d in 57-72% yield. Acid-catalyzed reaction of 5a-d with acetone, cyclopentanone, and cyclohexanone furnished 1,2,4-trioxepanes 8a-d, 9a-d, and 10a-d in good yields. Homoallylic alcohol 12 also underwent a highly regioselective photooxygenation to yield gamma-hydroxyhydroperoxide 13 in 67% yield, which on reaction with acetone, cyclopentanone, and cyclohexanone, furnished 1,2,4-trioxocanes 16-18 in 41-55% yield. |
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