Tetrahedron p. 3637 - 3648 (1999)
Update date:2022-08-05
Topics: Regioselectivity Yield Catalyst Rearrangement Cyclization Intermediate Aromaticity Intramolecular Reaction Nucleophilic Attack Reaction Mechanism Solvent Effects Activation Energy Spectroscopic Analysis Tautomerization Electrophilic addition Thermal reaction Oxazole
Clark, Adrian D.
Janowski, Wit K.
Prager, Rolf H.
Flash vacuum pyrolysis of 2-aroyl-3-phenylisoxazol-5(2H)-ones leads to good yields of 2-aryl-4-phenyloxazoles, and smaller quantities of 2-aryl-5- phenyloxazoles and 5-aryl-2-phenyloxazoles. The mechanism of formation of the 2,5-disubstituted products has been investigated by 13C and substituent labelling, and a non-statistical breakdown of a symmetrical intermediate is invoked to rationalise the product formation.
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Doi:10.1007/BF00764137
()Doi:10.1021/jm00303a011
(1969)Doi:10.1021/jacs.1c06757
(2021)Doi:10.1016/S0223-5234(99)80044-0
(1999)Doi:10.1039/c9cc06323d
(2019)Doi:10.1039/c8gc01886c
(2018)
