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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
| Authors and Corporations: | , , , |
|---|---|
| Title: |
Substituent effects of the cycloaddition reaction of 7-substituted 5H-benzocycloheptenes with singlet oxygen and the chemistry of the benzocycloheptene endoperoxides |
| In: | Canadian Journal of Chemistry, 83, 2005, 3, p. 227-235 |
| published: |
Canadian Science Publishing
|
| Physical Description: | 227-235 |
| ISSN: |
0008-4042 1480-3291 |
| DOI: | 10.1139/v05-046 |
| Summary: | <jats:p> 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 NEt<jats:sub>3</jats:sub> gave a mixture of products; hydroxyketone, diketone, and carboethoxy-substituted ketoenol 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.Key words: benzocycloheptene, photooxygenation, endoperoxides, rearrangement, CoTPP. </jats:p> |
| Type of Resource: | E-Article |
| Source: | Canadian Science Publishing (CrossRef) |
| Language: | English |