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Unusual manganese(III)-mediated oxidative free radical additions of 1,3-dicarbonyl compounds to benzonorbornadiene and 7-heterobenzonorbornadienes: Mechanistic studies

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dc.creator Caliskan, Rasit
dc.creator Ali, Mohamed Fadelalla
dc.creator Sahin, Ertan
dc.creator Watson, William H.
dc.creator Balci, Metin
dc.date 2007-04-26T21:00:00Z
dc.date.accessioned 2020-10-06T09:49:01Z
dc.date.available 2020-10-06T09:49:01Z
dc.identifier 448093ca-43ca-4247-8c5d-ad29edf830e1
dc.identifier 10.1021/jo0625711
dc.identifier https://avesis.sdu.edu.tr/publication/details/448093ca-43ca-4247-8c5d-ad29edf830e1/oai
dc.identifier.uri http://acikerisim.sdu.edu.tr/xmlui/handle/123456789/58736
dc.description 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.
dc.language eng
dc.rights info:eu-repo/semantics/closedAccess
dc.title Unusual manganese(III)-mediated oxidative free radical additions of 1,3-dicarbonyl compounds to benzonorbornadiene and 7-heterobenzonorbornadienes: Mechanistic studies
dc.type info:eu-repo/semantics/article


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