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

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Abstract

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.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    M. G. Voronkov, I. P. Tsyrendorzhieva & V. I. Rakhlin

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  1. M. G. Voronkov
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  2. I. P. Tsyrendorzhieva
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  3. V. I. Rakhlin
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Correspondence to V. I. Rakhlin.

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Original Russian Text © M.G. Voronkov, I.P. Tsyrendorzhieva, V.I. Rakhlin, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 4, pp. 487–489.

For communication X, see [1].

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Voronkov, M.G., Tsyrendorzhieva, I.P. & Rakhlin, V.I. Acyl iodides in organic synthesis: XI. Unusual N-C bond cleavage in tertiary amines. Russ J Org Chem 44, 481–484 (2008). https://doi.org/10.1134/S1070428008040015

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  • DOI: https://doi.org/10.1134/S1070428008040015

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