Manganese(III)-mediated oxidative free-radical additions of 1,3-dicarbonyl compounds to homobenzonorbornadiene and benzobarrelene: mechanistic studies

Date

2009-02-14

Author

Ali, Mohamed Fadelalla
Caliskan, Rasit Ali
ŞAHİN, Ertan
Balcı, Metin

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Homobenzonorbornadiene and benzobarrelene were reacted with dimedone/acetylacetone and Mn(OAc)(3) in the presence of Cu(OAc)(2) in acetic acid. Mainly rearranged products having a [2.2.2]skeleton and the nonrearranged dihydrofuran derivatives were obtained. These observations clearly indicated that the second oxidation takes place before the cyclization reaction. Furthermore, intramolecular tandem oxidations were observed where unusually oxyl radicals attack the double bond to form the products. The mechanism of the formation of the products is discussed.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/56473

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2008.12.012

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

M. F. Ali, R. A. Caliskan, E. ŞAHİN, and M. Balcı, “Manganese(III)-mediated oxidative free-radical additions of 1,3-dicarbonyl compounds to homobenzonorbornadiene and benzobarrelene: mechanistic studies,” TETRAHEDRON, pp. 1430–1437, 2009, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56473.