Pyrrolinone-pyrrolidinones

Treatment of the quaternary ammonium salt PhC=CCH2NMe2CH2COPh Br" with sodium hydroxide gives, inter alia, the betaine (98). Controlled-potential electrolysis of 7-nitro-ketones on a mercury cathode yields 1-pyrroline 1-oxides, pyrrolines, or pyrrolidines, according to conditions thus the oxide (99) is obtained from the compound 02NCMe2CHPhCH2C0Ph. The pyrrolinone (101) results from autoxidation of the furan derivative (100). Irradiation of the amide (102) leads to the pyrrolidinone (103) by an unprecedented [1,6] shift of hydrogen. " ... 

The allene PrCH=C=CHCH2NH2 isomerizes to the 3-pyrroline (122) under the influence of silver tetrafluoroborate. Photolysis of aroyl azides in the presence of diketen (123) yields the hydroxy-pyrrolinones (124).AT-Ray analysis has shown that the adduct of the imine Pr"CH=NPr to N-phenylmaleimide has structure (125). Treatment of dichloromaleimide with ethoxycarbonyl-methylenetriphenylphosphorane affords the Wittig product (126). The formation of the pyrrolidinone (128) in the thermolysis of the iV-cyclohexenylacryl-amide (127) represents an intramolecular ene-reaction (see arrows). The perfluoropyrrolidinone (130) results from the reaction of the cyclobutane (129) with potassium fluoride. Pyrrolidinols (131) are obtained in moderate yields by photochemical cyclization of the amides ArCOCH2CH2NBzCH2Ph. ... 

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