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.
点击下载:
PDF
(339KB)
返 回