Abstract
Abstract The present investigation was undertaken in order to see whether singlet oxygen-oxidation of unconjugated cyclic dienes having spatially close double bonds causes a particular transannular reaction as previously observed with 1,5-cyclooctadiene which gave 4-hydroxy-5-cyclooctenone. Most cyclic dienes tested underwent normal “ene” reaction to give allylic hydroperoxides. Thus, on dye-sensitized photooxygenation followed by reduction with sulfite, dicyclopentadiene, cis,trans-1,5-cyclodecadiene, trans,trans,trans1,5,9-cyclooctadiene, 1,4-cyclooctadiene, 1,3-cyclooctadiene and germacrone yielded a stereoisomeric mixture of tricyclo[5.2.1.02,6]decan-4,8-diene-3-ols, cis,cis-2,7-cyclodecadienol, a stereoisomeric mixture of two 2,5,9-cyclododecatrienols, 2,4-cyclooctadienol, endo-3,8-peroxide of cyclooctene, and germacra-3,7(11),10(14)-trien-9-ol-6-one(E), respectively. Under similar conditions, norbornadiene, and cis,cis-1,6-cyclodecadiene remained virtually unchanged.
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