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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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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.