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Synthesis of an α-amino nitrile and a bis α-amino nitrile derivative of thiadiazole: reaction mechanism.

Authors :
Mirífico, María Virginia
Caram, José Alberto
Piro, Oscar Enrique
Vasini, Enrique Julio
Source :
Journal of Physical Organic Chemistry; Dec2007, Vol. 20 Issue 12, p1081-1087, 7p, 4 Diagrams, 1 Chart, 4 Graphs
Publication Year :
2007

Abstract

The first nucleophilic addition of an inorganic nucleophile (cyanide) to the activated, rigid, α-diazomethine groups of a 1,2,5-thiadiazole 1,1-dioxide is reported here. An α-amino nitrile and a bis α-amino nitrile derivatives were obtained in good yields (62 and 98%, respectively) and characterized by spectroscopic, analytical, and single crystal X-ray diffraction techniques. The course of the reaction, followed by cyclic voltammetry (CV), showed that cyanide adds to only one of the two C&dbond;N double bonds of the thiadiazole, forming an anion from which an N-methyl derivative was obtained. Adequate concentrations of cyanide and methyl iodide (MeI) produced directly the bis α-amino nitrile derivative. Copyright © 2007 John Wiley & Sons, Ltd. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
08943230
Volume :
20
Issue :
12
Database :
Complementary Index
Journal :
Journal of Physical Organic Chemistry
Publication Type :
Academic Journal
Accession number :
27189418
Full Text :
https://doi.org/10.1002/poc.1257