Rearrangement of unsaturated cyclic peroxides obtained by photooxygenation of 2,3-dimethylene-7-oxabenzonorbornene and 2,3-dimethylene-1,4-etheno-1,2,3,4-tetrahydronaphthalene

Date

2001-08-27

Author

Ozen, R
Kormali, F
Balcı, Metin
Atasoy, B

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Cobalt(II) tetraphenylporphyrin (CoTPP)-catalyzed rearrangement of peroxide 11 obtained by the photooxygenation of 5 gave a mixture of epoxides 15 (or 16) and 17. However, CoTPP-catalyzed rearrangement of peroxide 20 arising by photooxygenation of 2,3-dimethylene-1,4-etheno-1,2,3,4-tetrahydronaphthalane 6 gave 1,4-etheno-1,2,3,4-tetrahydronaphtho[b]-furan 21. The different behaviour of these endoperoxides 11 and 20 is discussed in terms of ring strain and the degree of the pyramidalization of the C=C bond

Subject Keywords

Furan, Epoxide, Endoperoxide, Pyramidalized double bond, Carbomethoxylation

URI

https://hdl.handle.net/11511/52139

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/s0040-4020(01)00702-5

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

R. Ozen, F. Kormali, M. Balcı, and B. Atasoy, “Rearrangement of unsaturated cyclic peroxides obtained by photooxygenation of 2,3-dimethylene-7-oxabenzonorbornene and 2,3-dimethylene-1,4-etheno-1,2,3,4-tetrahydronaphthalene,” TETRAHEDRON, pp. 7529–7535, 2001, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/52139.