24455-26-3

Upstream product

• 140-89-6 potassium ethyl xanthogenate 
• 2028-84-4 p-methylbenzenediazonium chloride 
• 24455-24-1 S,S-di-p-tolyl ethanebis(thioate) 
• 106-45-6 para-thiocresol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 17241-10-0 tris(p-tolylthio)methane 
• 16754-59-9 tris-isopropylsulfanyl-methane 
• 108-98-5 thiophenol 
• 4832-52-4 tris(phenylthio)methane 
• 24455-28-5 di-4-tolyl trithiocarbonate 
• 75-44-5 phosgene 

Downstream Products

• 106-45-6 para-thiocresol 

Relevant academic research and scientific papers

A Mild Method for Access to α-Substituted Dithiomalonates through C-Thiocarbonylation of Thioester: Synthesis of Mesoionic Insecticides

An efficient method for targeting a variety of symmetrical and asymmetrical α-substituted dithiomalonates (DTMs) is described, utilizing 1H-imidazole-1-carbothioates as reactive acylating agents and MgBr2?OEt2/DBU or LiHMDS for soft or hard enolization conditions of thioesters, respectively. The utility of this methodology was demonstrated through the synthesis of the pyridopyrimidine mesoionic insecticides: triflumezopyrim and dicloromezotiaz. (Figure presented.).

Trithioorthoester Exchange and Metathesis: New Tools for Dynamic Covalent Chemistry

To expand the toolbox of dynamic covalent and systems chemistry, we investigated the acid-catalyzed exchange reaction of trithioorthoesters with thiols. We found that trithioorthoester exchange occurs readily in various solvents in the presence of stoichiometric amounts of strong Bronsted acids or catalytic amounts of certain Lewis acids. The scope of the exchange reaction was explored with various substrates, and conditions were identified that permit clean metathesis reactions between two different trithioorthoesters. One distinct advantage of S, S, S-orthoester exchange over O, O, O-orthoester exchange is that the exchange reaction can kinetically outcompete hydrolysis, thereby making the process less sensitive to residual moisture. We expect that the relatively high stability of the products might be beneficial in future supramolecular receptors or porous materials.

NOVEL DESULFURIZATION OF THIOCARBONYL COMPOUNDS INTO THEIR CARBONYL COMPOUNDS WITH TERTIARY BUTYL THIONITRATE

Various thiocarbonyl compounds such as thioamides, thiocarbamate, thiocarbonate, trithiocarbonate and thioketone were readily reacted with t-butyl thionitrate (t-BuSNO2) to give the corresponding carbonyl compounds in excellent yields under mild conditions.Desulfurization seems to be initiated via the selective nitrosation on the sulfur atom of thiocarbonyl group with t-BuSNO2.

THE REACTION OF t-BUTYL HYPOCHLORITE WITH THIOCARBONYL COMPOUND - A CONVENIENT METHOD FOR THE TRANSFORMATION

The reaction of t-butyl hypochlorite with different thiocarbonyl compounds has been studied.Primary thioamides 1a-c give 1,2,4-thiadiazole derivatives.N-Phenylthiourea 4a gives 5-imino-4-phenyl-3-phenylamino-4,5-dihydro-1,2,4-thiadiazoline 15.Secondary and tertiary thioamides 2a-d, N-methyl-2-thiopyrrolidinone 3, N,N'-dicyclohexylthiourea 4b, N,N,N'-trimethylthiourea 4c, 5-ethyl-5-phenylthiobarbituric acid 5, xanthione 7a, Mischler's thioketone 7b, thiocoumarin 8, O-ethylthiobenzoate 9, O,O-diphenylthiocarbonate 10, di-p-tolyl and o-phenylene trithiocarbonates 11 and 12 have all afforded the oxigen analogues.N,N-Dimethyl-S-phenyldithiocarbonate 6 produces a mixture of di-, tri-, and tetrasulfides.A mechanism for the transformation is suggested in accordance with the Hard and Soft Acids and Bases (HSAB) principle.

N-NITROSAMINES AS REAGENTS FOR THE =C=S=C=O TRANSFORMATION

N-nitrosopiperidine and N-nitroso-N-methylaniline react in acidic solution with thiocarbonyl compounds to give the corresponding carbonyl analogues.Secondary- and tertiary thioamides, xanthione, thio- and dithiobutyrolactone, thiocoumarin, certain thiourea derivatives, dithio-O,O-thiocarbonic, S,S-trithiocarbonic- and N,N disubstituted thiocarbamic esters are all converted into the corresponding O-analogues.Thiobenzamide and N-phenylthiourea yield 1,2,4-thiadiazoles.All the reactions are run with iodide (I-) as NO+-carrier.The kinetics of the reaction have been studied under pseudo-first order conditions, and the reaction rate is proportional to the Pearson's nucleophilicity parameter of ions.The =C=S =C=O transformation is also found to take place in gastric juice.

REACTION OF N,N'-THIONYLDIIMIDAZOLE WITH THIOLS: A SULFUR TRANSFER REACTION

Reaction of N,N'-thionyldiimidazole with thiols effects the formation of disulfides and trisulfides.These results are rationalized by assuming that the thiols react with N,N'-thionyldiimidazole to produce the disulfides and N,N'-thiobisimidazole which subsequently reacts with the starting thiols to give the trisulfides.