title: New rearrangement of 4-isoxazoline system: conversion of ketones into alpha,beta-unsaturated amides.
abstract: A new rearrangement pattern of the 4-isoxazoline system is reported. The reaction, starting from 3,3-disubstituted derivatives and leading to alpha,beta-unsaturated amides, proceeds through the quaternarization of the nitrogen atom and involves the heterolytic cleavage of C(3)-N bond, assisted by the formation of a relatively stable intermediate. The overall process represents a useful conversion of ketones into alpha,beta-unsaturated amides.
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Catania, Viale Andrea Doria 6, 95125 Catania, Italy. uchiacchio@dipchi.unict.it
authors.forename: Ugo
authors.initials: U
authors.lastname: Chiacchio
authors.forename: Antonio
authors.initials: A
authors.lastname: Rescifina
authors.forename: Maria Assunta
authors.initials: MA
authors.lastname: Chiacchio
authors.forename: Giovanni
authors.initials: G
authors.lastname: Romeo
authors.forename: Roberto
authors.initials: R
authors.lastname: Romeo