Synthesis of an α‐amino nitrile and a bis α‐amino nitrile derivative of thiadiazole: reaction mechanism |
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| Authors: | María Virginia Mirífico José Alberto Caram Oscar Enrique Piro Enrique Julio Vasini |
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| Institution: | 1. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA), Facultad de Ciencias Exactas, Departamento de Química, Universidad Nacional de La Plata, Casilla de Correo 16, Sucursal 4, (1900) La Plata, Argentina;2. Facultad de Ingeniería, Departamento de Ingeniería Química, Universidad Nacional de La Plata, Calle 47 y 1, (1900) La Plata, ArgentinaInstituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA), Facultad de Ciencias Exactas, Departamento de Química, Universidad Nacional de La Plata, Casilla de Correo 16, Sucursal 4, (1900) La Plata, Argentina.===;3. Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata and IFLP (CONICET), C. C. 67, 1900 La Plata, Argentina |
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| 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?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. |
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| Keywords: | nucleophilic addition thiadiazole heterocycles sequential reaction cyclic voltammetry X‐ray diffraction |
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