74199-51-2Relevant articles and documents
Partially Fluorinated Heterocyclic Compounds. Part 12. Novel Internal Diels-Alder Adducts via Claisen Rearrangement Intermediates from tetrafluoro-4- and -3-pyridyl Prop-2-enyl Ethers. Syntheses of Tetrafluoro-3-aza- and -4-aza-tricyclo2,7>non-3-en-6-one
Brooke, Gerald M.,Matthews, Raymond S.,Robson, Nigel S.
, p. 102 - 106 (2007/10/02)
Vapour-phase thermolyses of 2,3,5,6-tetrafluoro-4-pyridyl prop-2-enyl ether and 2,4,5,6-tetrafluoro-3-pyridyl prop-2-enyl ether gave 2,4,5,7-tetrafluoro-3-azatricyclo2,7>non-3-en-6-one (14) and 2,3,5,7-tetrafluoro-4-azatricyclo2,7>non-3-en-6-one (21) respectively by internal Diels-Alder reactions of Claisen rearrangement intermediates. 4-Bromo-2,3,5-trifluoro-6-pyridyl prop-2-enyl ether gave 4-bromo-3,5-difluoro-3-prop-2-enyl-pyridine-2,6(1H,3H)-dione (19) the product of hydrolysis of a Claisen intermediate.Compounds (14) and (21) underwent ready hydrolysis to the corresponding cyclic lactams, in which the ketonic carbonyl group at C-6 in both cases had also been converted into a gem-diol .Hydrolytic cleavage of (22) followed by oxidative cleavage with periodic acid and reaction with diazomethane gave a trimethoxycarbonyl compound (25) containing a difluorocyclobutane ring.
