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N-Nitromethylphthalimide. A formyl anion equivalent

 

作者: Frank G. Cowherd,   Marie-Carmen Doria,   Edvige Galeazzi,   Joseph M. Muchowski,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1977)
卷期: Volume 55, issue 16  

页码: 2919-2929

 

ISSN:0008-4042

 

年代: 1977

 

DOI:10.1139/v77-405

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

It is shown that the exclusive 1,4-addition ofN-nitromethylphthalimide4ato unhindered α,β-unsaturated ketones and esters can be effected by non-nucleophilic bases, such as sodium hydride or potassium fluoride, in dimethyl sulfoxide. The phthalimido moiety can be removed from the adducts with hydroxylamine or 1,2-dianilinoethane to give the oximes or diphenylimidazolidines of 1,4-ketoaldehydes. The ethylene ketal5of 3-formylcyclohexanone could easily be recovered from the imidazolidine10, but it was not possible to transform11into 3-formylcyclohexanone under similar conditions. It is further shown that reactions, such as the Knoevenagel condensation, or the Paal–Knorr synthesis of pyrroles, can be achieved directly on the adducts without the need for isolating the unstable 4-formyl carbonyl compounds.N-Nitromethylphthalimide thus serves as a new formyl anion equivalent.

 

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