Dithiocarbamates

Introduction

The dithiocarbamate functional group is an analogue of carbamate in which both oxygen atoms are replaced by sulfur atoms.

Figure 1

Organic dithiocarbamates have attracted attention because of their interesting chemistry and wide utility. They are valuable synthetic intermediates and their functionalization leads to the generation of derivatives which may possess diverse biological properties.

Dithiocarbamates are chain-transfer agents for RAFT polymerization,[1] and organic dithiocarbamates are used as substrates in radical chemistry[2] and as synthetic intermediates toward thioureas,[3] amidines[4] and guanidines.[5] They are highly versatile mono-anionic chelating ligands which form stable complexes with transition elements possessing applications in medicine.[6] Various dithiocarbamate salts can be easily prepared in high yields from amines, and they are soluble in water or organic solvents. Primary and secondary amines easily react with carbon disulfide and sodium hydroxide to form dithiocarbamate salts.

• References

• 1 Moad G, Rizzardo E, Thang SH. Aust. J. Chem. 2009; 62: 1402
• 2a Hartung J, Schur C, Kempter I, Gottwald T. Tetrahedron 2010; 66: 1365
• 2b Beckwith AL. J, Schiesser CH. Org. Biomol. Chem. 2011; 9: 1736
• 2c Schur C, Becker N, Bergstraesser U, Hartung J, Gottwald T. Tetrahedron 2011; 67: 2338
• 3 Alagarsamy V, Pathak US. Bioorg. Med. Chem. 2007; 15: 3457
• 4 Das P, Kiran Kumar C, Katari NK, Innus M, Iqbal J, Srinivas N. Tetrahedron Lett. 2008; 49: 992
• 5 Gobis K, Foks H, Zwolska Z, Augustynowicz-Kope E. Heterocycles 2010; 81: 917
• 6 Buac D, Schimitt S, Ventro G, Kona FR, Dou QP. Mini Rev. Med. Chem. 2012; 12: 1193
• 7 Halimehjani AZ, Ashouri A, Marjani K. J. Heterocyclic Chem. 2012; 49: 939
• 8 Halimehjani AZ, Pourshojaei BY, Saidi MR. Tetrahedron Lett. 2009; 50: 32
• 9 Katari NK, Sreeramamurthy BK, Palle AS, Mukkanti AK, Das P. Tetrahedron Lett. 2010; 51: 899
• 10 Lal N, Kumar L, Sarswat A, Jangir S, Sharma VL. Org. Lett. 2011; 13: 2330
• 11 Sun N, Li B, Shao J, Mo W, Hu B, Shen Z, Hu X. Beilstein J. Org. Chem. 2012; 8: 61
• 12 Nath J, Patel BK, Jamir L, Sinha UB, Satyanarayana KV. V. V. Green. Chem. 2009; 11: 1503