- Electrochemical oxidation of amides of type Ph2CHCONHAr
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Anodic oxidation of N-aryl-2,2-diphenylacetamides in acetonitrile undergoes three types of bond-cleavage, one between the benzylic carbon and the carbonyl group, the second between a carbonyl and 'N', and the third between the 'N' atom and aryl group. The selectivity of the cleavage and nature of emerged products is highly dependent on the nature of substituent attached to the aryl group. For example, electron-withdrawing groups direct the benzyl-carbonyl bond-breaking whereas electron-donating substituents favor the N-aryl bond cleavage. The type of products obtained involve benzophenone, 2,2-diphenylacetamide, N-(diphenylmethylene)acetamide, N-(diphenylmethyl)acetamide, α-lactam (1-acetyl-3,3-diphenylaziridin-2-one, as a 1:1 complex with 2,4-dinitroaniline) and aniline derivatives.
- Golub, Tatiana,Becker, James Y.
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experimental part
p. 3906 - 3912
(2012/06/04)
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- Site Selectivity in the Reaction of Formyl-2H-azirine-N-arylimines with Diphenylketene
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2-Formyl-2H-azirine-N-arylimines 1a-c react with diphenylketene 2 to afford 2H-2-azirinyl-2-azetidinones 3a-c and N-aryldiphenylacetamides 4a-c by reaction at the exo-imino group.Derivatives containing the bulkier methyl group at the 2-position, 1d-f, produce only 4a-c.
- Nunes, Jose,Kascheres, Albert
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p. 341 - 344
(2007/10/03)
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- REACTION OF DIPHENYLKETENE N-(p-TOLYL)IMINE WITH CARBOXYLIC ACIDS IN THE PRESENCE OF ARYLAMINES
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The reaction of diphenylketene p-tolylimine with carboxylic acids in aprotic organic solvents is accelerated by primary arylamines.The reaction rate is described by overall kinetic equation including calalytic and noncatalytic path.Additions of pyridine greatly retard the reaction.The proposal according to which the catalytic reaction takes place through a cyclic transition state, formed from the ketene imine and the complex of the carboxylic acid with the amine, was substantiated.
- Mironova, D. F.,Loginova, N. A.
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p. 2344 - 2348
(2007/10/02)
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- ADDITION AT THE C=N BOND IN KETENE IMINES. REACTION OF DIPHENYLKETENE N-(p-TOLYL)IMINE WITH N,N-DIMETHYLDICHLOROMETHYLENEAMMONIUM CHLORIDE
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Electrophilic addition to arylketene imines at the C=N bond is described for the reaction of diphenylketene N-(p-tolyl)imine with N,N-dimethyldichloromethyleneammonium chloride.Chlorinating characteristics were found in the complex of N,N-dimethyldichloromethyleneammonium chloride with chlorine.
- Mironova, D. F.,Vykhrestyuk, N. I.,Kukhar', V. P.
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p. 242 - 245
(2007/10/02)
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