Regioselectivity in the ene-reaction of singlet oxygen with cyclic alkenes: photooxygenation of methyl-substituted 1,4-cyclohexadiene derivatives

Date

2006-11-13

Author

Yardimci, Sengul Dilem
Kaya, Nihal
Balcı, Metin

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The photooxygenation of the 1-methyl-, 2,3-dimethyl-, and 1,4-dimethylcyclohexa-1,4-dienes, which are readily available through Birch reduction, yielded the corresponding ene-products. The formed endocyclic dienes were trapped by the addition of singlet oxygen to give the corresponding bicyclic endoperoxy hydroperoxides. In the case of 1-methylcyclohexa-1,4-diene and 1,4-dimethylcyclohexa-1,4,-diene, the cis-effect determined the product distribution. Photooxygenation of 2,3-dimethylcyclohexa-1,4-dienes gave mainly exocyclic olefin, which was attributed to the lowered rotational barrier of the methyl group and increased reactivity of the methyl groups.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/57224

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2006.07.103

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Graduate School of Natural and Applied Sciences, Article

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Citation Formats

S. D. Yardimci, N. Kaya, and M. Balcı, “Regioselectivity in the ene-reaction of singlet oxygen with cyclic alkenes: photooxygenation of methyl-substituted 1,4-cyclohexadiene derivatives,” TETRAHEDRON, pp. 10633–10638, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57224.