267877-39-4Relevant articles and documents
High-temperature rearrangements of 2-acylisoxazol-5(2H)-ones and related oxazoles
Clark, Adrian D.,Ha, Uyen T.,Prager, Rolf H.,Smith, Jason A.
, p. 1029 - 1033 (2007/10/03)
2-Acyl-3-arylisoxazol-5(2H)-ones give 2-alkyl(aryl)-4-aryloxazoles in good yields at 540°C under flash vacuum pyrolysis conditions, but at higher temperatures the expected oxazoles are accompanied by increasing amounts of isomeric 2,5-disubstituted oxazoles, as well as anilides and decomposition products of the 2,4-disubstituted oxazole. The rearrangement mechanisms have been studied by the use of 13C labelled substrates and p-substituted 3-arylisoxazolones. The 2,5-disubstituted oxazoles are considered to arise from 1H-azirines, and the anilides from the nitrone ketene isomer of the acylisoxazolone.
