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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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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.