Acyl iodides in organic synthesis: XI. Unusual N-C bond cleavage in tertiary amines

Acyl iodides reacted with excess primary and secondary amines in a way similar to acyl chlorides, yielding the corresponding carboxylic acid amide and initial amine hydroiodide. Reactions of tertiary amines with acyl iodides were accompanied by cleavage of the N-C bond with formation of the correspo...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2008-04, Vol.44 (4), p.481-484
Main Authors: Voronkov, M. G., Tsyrendorzhieva, I. P., Rakhlin, V. I.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:Acyl iodides reacted with excess primary and secondary amines in a way similar to acyl chlorides, yielding the corresponding carboxylic acid amide and initial amine hydroiodide. Reactions of tertiary amines with acyl iodides were accompanied by cleavage of the N-C bond with formation of the corresponding N,N -di(hydrocarbyl)carboxamide and alkyl iodide. In the presence of excess tertiary amine the latter was converted into quaternary tetra(hydrocarbyl)ammonium iodide.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428008040015