917100-73-3Relevant academic research and scientific papers
Synthesis of 1,2,4-trioxepanes and 1,2,4-trioxocanes via photooxygenation of homoallylic alcohols
Singh, Chandan,Pandey, Shilpi,Saxena, Gunjan,Srivastava, Nisha,Sharma, Malvika
, p. 9057 - 9061 (2007/10/03)
(Chemical Equation Presented) Homoallylic alcohols 4a-d, easily accessible in two steps from cyclopropyl methyl ketone, underwent a highly regioselective reaction with singlet oxygen to yield γ-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 δ-hydroxyhydroperoxide 13 in 67% yield, which on reaction with acetone, cyclopentanone, and cyclohexanone, furnished 1,2,4-trioxocanes 16-18 in 41-55% yield.
