Acyl iodides in organic synthesis. Reactions with morpholine,piperidine, and N-hydrocarbylpiperidines |
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Authors: | M. G. Voronkov I. P. Tsyrendorzhieva V. I. Rakhlin |
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Affiliation: | 1.Favorskii Irkutsk Institute of Chemistry, Siberian Division,Russian Academy of Sciences,Irkutsk,Russia |
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Abstract: | Acyl iodides RCOI (R = Me, Ph) reacted with morpholine and piperidine to give the corresponding N-acyl derivatives and morpholine or piperidine hydroiodides. Reactions of acyl iodides with N-methyl- and N-ethylpiperidines involved cleavage of the exocyclic R-N bond with formation of N-acylpiperidine and alkyl iodide and were accompanied (to insignificant extent) by cleavage of the endocyclic N-C bond, leading to N-alkyl-N-(5-iodopentyl)acylamides. In the reaction of acetyl iodide with N-phenylpiperidine, the main process was cleavage of just endocyclic N-C bond to produce N-(5-iodopentyl)-N-phenylacetamide and its dehydroiodination product, N-(pent-4-en-1-yl)-N-phenylacetamide. Analogous reaction with benzoyl iodide afforded N-(5-iodopentyl)-N-phenylbenzamide in a poor yield. |
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