Reactions of carbon disulfide with N-nucleophiles

Unexpected formation of ammonium thiocyanate from the reaction of aqueous hydroxylamine with carbon disulfide

“…The LCMS recorded after 5 h showed few more less intense signal with higher m/z value (see Supplementary information). Based on our observations as well as reports on similar reactions [7,16], we propose to explain the formation of ammonium thiocyanate and sulfur as shown in Scheme 1. The formation of hydroxylthiourea shown in the step 1 of the mechanism is well established in similar reactions [7,11,16].…”

“…Synthetic utility of the reactions between carbon disulfide and Nnucleophiles to form wide range of organosulfur compounds are well known [7]. Carbon disulfide is known to deoxygenate tertiary amine N-oxides to tertiary amines [8] and N, N-disubstituted hydroxylamines to secondary amines [9].…”

“…Hydroxylamine is used as reducing agents in a variety of organic and inorganic reactions [1][2][3]. Further, hydroxylamine nitrate (HAN), a derivative of hydroxylamine has been used for applications that include equipment decontamination in nuclear industry and also as aqueous or solid propellants [4][5][6].Synthetic utility of the reactions between carbon disulfide and Nnucleophiles to form wide range of organosulfur compounds are well known [7]. Carbon disulfide is known to deoxygenate tertiary amine N-oxides to tertiary amines [8] and N, N-disubstituted hydroxylamines to secondary amines [9].…”

Hydrazinecarbothioamide group in the synthesis of heterocycles

“…In pyridine, reaction of 2 with carbon disulfide afforded the salts 75 and 76. 56 In DMF, compound 2 reacted with carbon disulfide and KOH to afford the salt 77 which can be cyclized on warming to give the corresponding 1,3,4-thiadiazoline-2-thione (Scheme 38). …”

Synthesis, characterization and biological activity of some nickel(II) mixed ligands complexes of dithiocarbamate and 1,10-phenanthroline

“…Dithiolates are formed when nucleophiles attack carbon disulphide [1]. There are some reports for synthesis of DTC derivatives in the literature [6][7][8][9], also there is a substantial interest in developing efficient one-pot-three component reaction from a simple starting materials (amines, carbon disulfide and epoxides) in novel reaction media such as water and ionic liquid [10][11][12][13]. These 1,1-dithiolate systems are of current interest due to their potential biological activity and practical application in the field of rubber technology and agriculture in addition to general consideration of metalsulfate bonding and electron delocalization in transition of metal complexes [14,15].…”