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, 15N, and 13C 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 occurrence 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.
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|Titolo:||Reaction Mechanisms of Gaseous Organic Cations. 20. Reactivity of Ionized 3-Phenylisoxazol-5-(4h)-One|
|Data di pubblicazione:||1981|
|Citazione:||Reaction Mechanisms of Gaseous Organic Cations. 20. Reactivity of Ionized 3-Phenylisoxazol-5-(4h)-One / Uccella, N; Liguori, Angelo; Sindona, Giovanni. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 46:12(1981), pp. 4450-4453.|
|Appare nelle tipologie:||1.1 Articolo in rivista|