Reactions of Nitroalkenes with Nitroalkanes or Sulfur Ylides Catalyzed by Amine-Thiourea Bifunctional Polymeric Organocatalysts

Abstract

Non-cross-linked and cross-linked bifunctional polystyrenes bearing both amine and thiourea groups have been synthesized and used as organocatalysts in reactions between nitroalkenes and nitroalkanes or sulfur ylides. Control experiments using monofunctional polymers with only either amine or thiourea groups attached indicated that both functional groups were essential for efficient catalysis of the reactions studied. The non-cross-linked polystyrene was soluble in typical organic solvents and was used as a homogeneous catalyst, while the cross-linked polystyrene was used as a heterogeneous catalyst.