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Reactions with Hexafluoroacetone Azine, XXII. - Reaction Behaviour of Hexafluoroacetone Azine towards Enol Ethers and Enamines
Burger, Klaus,Hein, Friedrich
, p. 853 - 871 (2007/10/02)
Hexafluoroacetone azine (1) reacts with enol ethers to give 1,3-cycloadducts.The azomethine imines 3 and 19a formed by reaction of 1 with vinyl ethers are capable to undergo a second cycloaddition step to give "criss-cross" cycloadducts (4,5,20).Contrary, the azomethine imines 14 and 19b derived from α-substituted enol ethers undergo heterolytic ring opening.The 1,x-dipoles formed spontaneously undergo a prototropic rearrangement to give hexafluoroacetone hydrazones (16, 17, 21). - In the reaction of 1 with enamines only for trans-N-(1-propenyl)piperidine a 1,3-cycloadduct can be detected spectroscopically at -15 deg C.Open chain as well as cyclic enamines having a β-hydrogen atom react to give hydrazones (25, 26, 28, 29).Enamines without hydrogen atoms in β-position and 1 in a cycloaddition process yield azetidines 33.
