Unsaturated nitrogen compounds containing fluorine. Part 12. Reaction of 2--1,1,1,3,3,3-hexafluoropropan-2-ide with monosubstituted ethenes, chlorine and hydrogen chloride

Article abstract of DOI:10.1016/0022-1139(93)02912-X

Treatment of the title azomethinimine (1) with alkenes CH2=CHR (R = CO2H, CHO, OCH3, CH2Br, CH2Cl and OCH2CH2Cl) and dienes CH2=CRCR=CH2 (R = H or Me) results in the regiospecific formation of the 2-substituted <3+2> cycloadducts in which the CHR group of the alkene is bonded to the nitrogen of the azomethinimine; with isoprene, major addition involves the CH2=CH- grouping.Reaction with chlorine affords a mixture of the dienes (CF3)2C=NNHC(CF3)2CH2CMe=CH2, (CF3)2CClN=NC(CF3)2CH2CMe=CH2 and (CF3)2CClN=NC(CF3)2CH2C(CH2Cl)=CH2, while with hydrogen chloride the diene (CF3)2C=NNHC(CF3)2CH2CMe=CH2 and an adduct, possibly (CF3)2CHN=NC(CF3)2CH2CMe2Cl, are formed.