
TY  - JOUR
A1  - Clark, Adrian D. 
A1  - Ha, Uyen T. 
A1  - Prager, Rolf H. 
A1  - Smith, Jason A. 
T1  - High-Temperature Rearrangements of 2-Acylisoxazol-5(2<emph type="2">H</emph>)-ones and Related Oxazoles.
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2000
VL  - 52
IS  - 11
SP  - 1029
EP  - 1034
KW  - 
UR  - https://doi.org/10.1071/CH99075 
N2  - 2-Acyl-3-arylisoxazol-5(2H)-ones give 2-alkyl(aryl)-4-aryloxazoles in good yields at 540&#176;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. 
ER  -

