Tetrahedron

Unusual Rearrangements of 2-aroylimidoyl-2-phenylethylidene to 2, 5-disubstituted Oxazoles

AD Clark, WK Janowski, RH Prager

文献索引：Clark, Adrian D.; Janowski, Wit K.; Prager, Rolf H. Tetrahedron, 1999 , vol. 55, # 12 p. 3637 - 3648

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被引用次数: 11

摘要

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.