Some further reactions of bis(trifluoromethyl)amino-oxyl with alkenes

Article abstract of DOI:10.1016/0022-1139(94)03073-1

The reaction of the oxyl (CF3)2NO^. (1) with the alkene (2) at 100 deg C and with the alkenes (CF3)2NCF2CF=CF2 (3), (E)-PhCH=CHPh (4), CH2=CHCOCl (5) and (CF3)2NCF2CF=CFCF2ON(CF3)2 (6) (prepared in 76percent yield by reaction of the oxadiazapentane (CF3)2NON(CF3)2 (7) with the diene CF2=CFCF=CF2) at room temperature gave high yields (92percent - 100percent) of the corresponding 2:1 adducts 8-12; hydrolysis of the acid chloride 11 gave the acid 14 (100percent).A mixture of the oxyl 1 and 3-bromopropene (4:5 molar ratio) on reaction at room temperature afforded at complex mixture of products of which the major compounds were identified by GLC-MS as (CF3)2NCH2CH=CH2 (15), (CH2Br)2CHON(CF3)2 (16), (CF3)2NOCH2CH(CH2Br)ON(CF3)2 (17), (CF3)2NCH2CH(CH2Br)ON(CF3)2 (18) and possibly <(CF3)2NOCH2>2CHBr (19).The following order of reactivity of ethenes towards oxyl 1 attack was obtained; CH2=CCl2 > CHF=CF2 > CHCl=CCl2 > CH2=CHCl > CH2=CH2 > CH2=CHF > CH2=CF2 > CCl2=CCl2. - Keywords: Reactions; Bis(trifluoromethyl)amino-oxyl; Alkenes; NMR spectroscopy; IR spectroscopy; Mass spectrometry