Chemistry of dioxine-annelated cycloheptatriene endoperoxides and their conversion into tropolone derivatives: an unusual non-benzenoid singlet oxygen source

Date

2006-04-24

Author

Dastan, A
Balcı, Metin

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The chemistry of two bicyclic endoperoxides, obtained by photooxygenation of 2,3-dihydro-7H-cyclohepta[1,4]dioxine and 2,3-dihydro-7H-cyclohepta[b][1,4]dioxin-7-one was investigated with the aim of synthesizing the respective tropolone derivatives. The reaction of these endoperoxides with base, thiourea and their thermolysis provided the desired tropolone derivatives in high yield. On the other hand, the thermolysis of the endoperoxide derived from 2,3-dihydro-7H-cyclohepta[b] [ 1,4]dioxin-7-one underwent an unprecedented route and formed parent Molecule and singlet oxygen instead of the expected troponoids. The formation mechanisms of all products are discussed.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/56791

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2006.02.026

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

A. Dastan and M. Balcı, “Chemistry of dioxine-annelated cycloheptatriene endoperoxides and their conversion into tropolone derivatives: an unusual non-benzenoid singlet oxygen source,” TETRAHEDRON, pp. 4003–4010, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56791.