78698-25-6Relevant academic research and scientific papers
Reaction Mechanisms of Gaseous Organic Cations. 20. Reactivity of Ionized 3-Phenylisoxazol-5(4H)-one
Liguori, Angelo,Sindona, Giovanni,Uccella, Nicola
, p. 4450 - 4453 (1981)
The chemistry of ionized 3-phenylisoxazol-5(4H)-one, which is relatively slow reacting in the gas phase, has been investigated by analysis of the mass-analyzed ion kinetic energy spectrum (MIKES), kinetic energy release, appearance energy, exact mass measurements and D, (15)N, (13)C labeling.Appropriate experiments show that the N,O-heterocyclic radical cations under study undergo unimolecular dissociations leading to the formation of benzoyl and formanilinium cations through pathways which involve phenyl migration.PhCO+ fragment ion formation must occur through a reaction channel akin to a thermochemical process.This implies a deep skeletal reorganization similar to an electrophilic substitution onto the aromatic ring and excludes the occurence of photochemical-like activation giving rise to isoxazole-oxazole ring isomerization.The decomposing ions possess, therefore, only a small excess energy, and have to follow only low-lying reaction channels.
Unusual rearrangements of 2-aroylimidoyl-2-phenylethylidene to 2,5- disubstituted oxazoles
Clark, Adrian D.,Janowski, Wit K.,Prager, Rolf H.
, p. 3637 - 3648 (2007/10/03)
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.
