Electrogenerated Base-Promoted Synthesis of Dithiocarbamate Acid Esters and 3-(N-Substituted-amino)-2-cyanodithiocrotonates from Primary or Secondary Amines and Carbon Disulfide

Authors: Toumi, Meriem¹; Raouafi, Noureddine¹; Boujlel, Khaled¹; Tapsoba, Issa²; Picard, Jean-Paul³; Bordeau, Michel³

Source: Phosphorus, Sulfur, and Silicon and the Related Elements, Volume 182, Number 10, October 2007 , pp. 2477-2490(14)

Publisher: Taylor and Francis Ltd

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Abstract:

Electrogenerated cyanomethyl anion promotes the reaction between primary or secondary amines, carbon disulfide, and alkyl or benzyl halide. Secondary amines are converted to alkyl or benzyl dithiocarbamates, whereas primary amines give N-substituted alkyl or benzyl 3-amino-2-cyanodithiocrotonates. The mechanisms are discussed.

Keywords: 3-(N-substituted-amino)-2-cyanodithiocrotonates; carbon disulfide; cyanomethyl dithiocarbamates; anion; EGBs

Document Type: Research article

DOI: http://dx.doi.org/10.1080/10426500701501607

Affiliations: 1: Laboratoire de Chimie Analytique et Electrochimie, Faculté des Sciences de Tunis, Campus Universitaire, Tunis El Manar, Tunisie 2: Laboratoire d'Activation Moléculaire et de Réactivité Electrochimique, Ecole Normale Supérieure, Paris, France 3: Laboratoire de Chimie Organique et Organométallique, Université Bordeaux, Talence, France

Publication date: 2007-10-01