A reaction of thioamides with zinc ammoniates leading to simple amidines. discovery of a new zwitterionic monomethylamidine

The reacion of thioamides with the R1R2N–ZnCl ammoniates leads to N-mono-, N,N′-di-, N,N-disubstituted, and unsubstituted amidines with high concentrations of amines in absolute ethanol. The efficient direct formation of the N,N′-dimethylamidine can be explained by a greater reactivity of methylamin...

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Bibliographic Details
Published in:Catalysis letters 2006-06, Vol.109 (1-2), p.55-60
Main Author: SPYCHALA, Jarostaw
Format: Article
Language:English
Subjects:
Amines
Carbonyls
Catalysis
Chemistry
Ethanol
Exact sciences and technology
General and physical chemistry
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Thymine
Zwitterions
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Summary:The reacion of thioamides with the R1R2N–ZnCl ammoniates leads to N-mono-, N,N′-di-, N,N-disubstituted, and unsubstituted amidines with high concentrations of amines in absolute 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.
ISSN:1011-372X
1572-879X
DOI:10.1007/s10562-006-0056-4