The activation of elemental sulfur (S(8)) has been achieved by means of electrogenerated cyanomethyl anion [easily obtained by galvanostatic reduction from acetonitrile/tetraethylammonium hexafluorophosphate (MeCN-Et(4)NPF(6))]. The "activated" sulfur reacted with ylidenernalononitriles to give substituted 2-aminothiophenes in very high yields. This variation of the Gewald reaction has been carried out using only catalytic amounts of electricity and supporting electrolyte. A proposed mechanism for the interaction between S(8) and cyanomethyl anion is described.
Activation of Elemental Sulfur by Electrogenerated Cyanomethyl Anion: Synthesis of Substituted 2-Aminothiophenes by the Gewald Reaction
Isabella Chiarotto;
2008
Abstract
The activation of elemental sulfur (S(8)) has been achieved by means of electrogenerated cyanomethyl anion [easily obtained by galvanostatic reduction from acetonitrile/tetraethylammonium hexafluorophosphate (MeCN-Et(4)NPF(6))]. The "activated" sulfur reacted with ylidenernalononitriles to give substituted 2-aminothiophenes in very high yields. This variation of the Gewald reaction has been carried out using only catalytic amounts of electricity and supporting electrolyte. A proposed mechanism for the interaction between S(8) and cyanomethyl anion is described.File in questo prodotto:
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