Some aliphatic carboxylic anhydrides gave excellent yields of the novel addition products to both aliphatic and aromatic N-methyleneimines, starting from their aliphatic and aromatic trimeric cyclic oligomers. A preliminary positive ion mass spectrometric study is here reported. They hydrolyze surprisingly faster than the corresponding acid amides, making necessary the intervention of a special mechanism. The reduction of the acetylamideester of cyclohexylmethyleneimine (3c) with LiAlH4 was also “abnormal”, as it yielded N-methyl-N-ethylcyclohexylamine in quantitative yield.

Revisitation of the reaction between Aniline and Formaldehyde. 6. The Accumulated Amide Ester Function from Addition of Carboxylic Anhydrides to N-Methyleneamines or their Trimers.

VERARDO, Giancarlo;CAUCI, Sabina
1987

Abstract

Some aliphatic carboxylic anhydrides gave excellent yields of the novel addition products to both aliphatic and aromatic N-methyleneimines, starting from their aliphatic and aromatic trimeric cyclic oligomers. A preliminary positive ion mass spectrometric study is here reported. They hydrolyze surprisingly faster than the corresponding acid amides, making necessary the intervention of a special mechanism. The reduction of the acetylamideester of cyclohexylmethyleneimine (3c) with LiAlH4 was also “abnormal”, as it yielded N-methyl-N-ethylcyclohexylamine in quantitative yield.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11390/718038
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