Etude du comportement de benzoxazinones, substituees en position 2 par des groupements (per)halogenes, vis-a-vis de l'aniline

Article abstract of DOI:10.1016/S0022-1139(00)82790-6

This study describes firstly the synthesis of benzoxazinones substituted in position 2 by halogenated groups such as -(CH2)n-R_F,Cl where n=0, 1 and 2 and R_F,Cl is a perhalogenated group, and secondly the reaction of these new benzoxazinones with aniline in different media.Thus it is shown that the behaviour of trifluoromethyl-2-benzoxazinone towards aniline is different, in most cases, in comparison with benzoxazinones substituted by perfluorinated groups CnF2n+1 with n=2, 3 and 7.Under certain conditions (hot ethanol and aniline with triphenyl phosphite), it is observed that nucleophilic attack of aniline only occurs on the carbonyl group when benzoxazinones are substituted by an electron-withdrawing group such as C2F5, C3F7 and C7F15.