292605-27-7Relevant articles and documents
Revisiting the addition of nitriloxides on protoanemonin. A new access to (2E)-3-(3'-arylisoxazol-5'-yl)propenoic acids
Roussel, Christophe,Fihi, Rachid,Ciamala, Kabula,Audebert, Pierre,Vebrel, Joel
, p. 471 - 476 (2007/10/03)
Some 4-substituted arylnitriloxides undergo 1,3-dipolar cycloadditions with 5-methylene(5H)furan-2-one (protoanemonin) with formation of spiroisoxazolines. These spiroadducts can be opened to the corresponding (2E)3-(3'-arylisoxazol-5'-yl)propenoic acids 5 and 3-aryl-5[4'-(3'-aryl- 4',5'-dihydroisoxazolinyl)]isoxazole 6 by various ways, including acidic and basic treatments, as well as electrooxidation. In the latter case, the electron transfer occurs on the 4,5-dihydroisoxazolic ring and is followed by an internal dissociative electron transfer leading to the opened products.