Bulletin des Soc Chimique

1993

DOI: 10.1002/bscb.19931020208

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Condensation of Dichloromethyleniminium Chloride with Alkylidenemalononitriles or Alkylidenecyanoacetates

Abstract: Phosgeniminium salt 1 easily condenses with vinylogues of malononitrile to yield new y,yrdicyano-a-chlorodienamines Lz which can undergo substitutions and heterocyclisation reactions.Viny1ogues of malonate do not react with 1 whereas those of cyanoacetate 21 lead to the formation of new a-pyrones 2.

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Cited by 11 publications

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N-Dichloromethylene-N,N-dimethyliminium Chloride

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2001

Encyclopedia of Reagents for Organic Synthesis

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N-Dichloromethylene-N,N-dimethyliminium Chloride

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²

2001

Encyclopedia of Reagents for Organic Synthesis

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ChemInform Abstract: Condensation of Dichloromethyleniminium Chloride with Alkylidenemalononitriles or Alkylidenecyanoacetates.

1993

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1993nitriles nitriles (acyclic compounds) P 0350 -126Condensation of Dichloromethyleniminium Chloride with Alkylidenemalononitriles or Alkylidenecyanoacetates.-Condensation of the title compound (II) with malonodinitriles, e.g. (I) , easily yields the new compounds (III), which are stable in neutral aqueous solution, due to their stabilizing push-pull conjugation. They undergo chlorine substitution by various nucleophilic reagents, e.g. to (V) with inversion of configuration, and heterocyclization reactions, e.g. to (VI) and, with loss of malononitrile, to (VIII) and (IX). Condensation of (II) with alkylidenecyanoacetates (X) is also accomplished, yielding new pyrones of type (XII) by immediate cyclization of the intermediates (XI), while condensation with the corresponding malonodiesters does not take place under these conditions. -(BOUVY, D.; JANOUSEK, Z.; VIEHE, H. G.; Bull.

Push-pull-Butadiene. XIII. Reaktionen von 3-Aryl-2-cyano-5,5-bis(methylthio)penta-2,4-diennitrilen mit Aminen

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1994

J. Prakt. Chem.

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