Substituent effects of the cycloaddition reaction of 7-substituted 5H-benzocycloheptenes with singlet oxygen and the chemistry of the benzocycloheptene endoperoxides

Date

2005-03-01

Author

Guney, M
Ceylan, ZC
Dastan, A
Balcı, Metin

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The cycloaddition reaction of 7-substituted 5H-benzocycloheptenes with singlet oxygen and the chemistry of the obtained endoperoxides were investigated. Reaction of carboethoxy-substituted endoperoxide with NEt3 gave a mixture of products; hydroxyketone, diketone, and carboethoxy-substituted keto-enol tautomers, whereas the reaction of methyl-substituted endoperoxide only formed a diketone under the same reaction conditions. Thermolysis, thiourea, and CoTPP reactions of the endoperoxides were also studied. The reaction mechanism and electronic effect of substituents were discussed.

Subject Keywords

Organic Chemistry, General Chemistry, Catalysis

URI

https://hdl.handle.net/11511/56527

Journal

CANADIAN JOURNAL OF CHEMISTRY

DOI

https://doi.org/10.1139/v05-046

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

M. Guney, Z. Ceylan, A. Dastan, and M. Balcı, “Substituent effects of the cycloaddition reaction of 7-substituted 5H-benzocycloheptenes with singlet oxygen and the chemistry of the benzocycloheptene endoperoxides,” CANADIAN JOURNAL OF CHEMISTRY, pp. 227–235, 2005, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56527.