Unusual oxidative free-radical additions of 1,3-dicarbonyl compounds to benzonorbornadiene and oxabenzonorbornadiene

Date

2005-09-12

Author

Cahskan, R
Pekel, T
Watson, WH
Balcı, Metin

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Benzonorbornadiene and oxabenzonorbornadiene were reacted with dimedone and acetylacetone in the presence of Mn(OAc)(3) and Cu(OAc)(2). The reaction of benzonorbornadiene with dimedone gave the dihydrofuran addition product, whereas the reaction with acetylacetone produced, in addition to the dihydrofuran derivative, a rearranged product. On the other hand, oxanorbornadiene gave unusual products such as the cyclopropanated compound and the product arising from the addition of two moles of dimedone. The mechanism of formation of the products is discussed.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/50637

Journal

TETRAHEDRON LETTERS

DOI

https://doi.org/10.1016/j.tetlet.2005.07.051

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

R. Cahskan, T. Pekel, W. Watson, and M. Balcı, “Unusual oxidative free-radical additions of 1,3-dicarbonyl compounds to benzonorbornadiene and oxabenzonorbornadiene,” TETRAHEDRON LETTERS, pp. 6227–6230, 2005, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/50637.