Tetrahedron

Photoinduced reactions—XLIX: Photosensitized oxygenation of cis, cis-1, 5-cyclooctadiene and cis-cyclooctene

T Matsuura, A Horinaka, H Yoshida, Y Butsugan

文献索引：Matsuura,T. et al. Tetrahedron, 1971 , vol. 27, p. 3095 - 3100

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被引用次数: 8

摘要

Rose bengal-sensitized photooxygenation of cis, cis-1, 5-cyclooctadiene (I) in methanol followed by reduction with sodium sulfite gave 2, 5-cyclooctadienol (II) and 4-hydroxy-5- cyclooctenone (III). The latter product was found to result from an unusual transannular reaction of the initially formed hydroperoxide, 6-hydroperoxy-1, 4-cyclooctadiene (VIII). Under similar conditions cis-cyclooctene (IX) gave 2-cyclooctenol (X). 1, 5-Cyclooctadiene ...