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Unusual manganese(III)-mediated oxidative free radical additions of 1,3-dicarbonyl compounds to benzonorbornadiene and 7-heterobenzonorbornadienes: Mechanistic studies
Date
2007-04-27
Author
Caliskan, Rasit
Ali, Mohamed Fadelalla
Sahin, Ertan
Watson, William H.
Balcı, Metin
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Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
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Benzonorbornadiene and heterobenzonorbornadiene were reacted with dimedone/acetylacetone and Mn(OAc)3 in the presence and absence of Cu(OAc)2. The reaction of benzonorbornadiene with dimedone gave mainly the dihydrofuran addition product, whereas the reaction with acetylacetone produced a rearranged product in addition to the dihydrofuran derivative. On the other hand, oxanorbornadiene gave unusual products such as the cycloproponated compound and a product arising from the incorporation of 2 mol of dimedone. The reaction of azanorbornadiene with 1,3-dicarbonyl compounds and Mn(OAc)3 always produced rearranged products. The mechanism of formation of the products is discussed. We generally observe that the cyclization reaction takes place after the oxidation of the initially formed radical.
Subject Keywords
Organic Chemistry
URI
https://hdl.handle.net/11511/52350
Journal
JOURNAL OF ORGANIC CHEMISTRY
DOI
https://doi.org/10.1021/jo0625711
Collections
Graduate School of Natural and Applied Sciences, Article