Convenient Syntheses of N-Methylthioamides: A Migration of the H2S Molecule in the Thioamide-nitrile System

Jaroslaw Spychala

doi:https://doi.org/10.1080/17415990600654599

Convenient Syntheses of N-Methylthioamides: A Migration of the H2S Molecule in the Thioamide-nitrile System

Abstract

The reaction of thioamides with the R1R2N-ZnCl ammoniates leads to N-mono-, N,N'-di-, N,N-disubstituted, and unsubstituted amidines with high concns. of amines in abs. ethanol. The efficient direct formation of the N,N'-dimethylamidine can be explained by a greater reactivity of methylamine compared with dimethylamine. Discovery of a new zwitterion (induced by a carbonyl oxygen) suggests that the stabilization in the thymine N-methylamidine is too slight to prevent the subsequent reaction with methylamine.

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Jaroslaw Spychala dr

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Category:: Magazine publication
Type:: Magazine publication
Published in:: Journal of Sulfur Chemistry no. 27, edition 3, pages 203 - 212,
ISSN: 1741-5993
Title of issue:: JOURNAL OF SULFUR CHEMISTRY strony 203 - 212
Publication year:: 2006
Bibliographic description:: Jaroslaw Spychala, Convenient Syntheses of N-Methylthioamides: A Migration of the H2S Molecule in the Thioamide-nitrile System, Journal of Sulfur Chemistry, vol. 27(3), pages 203-212, 2006.
DOI:: Digital Object Identifier (open in new tab) https://doi.org/10.1080/17415990600654599
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