623-54-1

Usage

Synthesis Reference(s)

Synthetic Communications, 19, p. 547, 1989 DOI: 10.1080/00397918908050698

InChI:InChI=1/C4H8OS2/c1-3-5-4(6)7-2/h3H2,1-2H3

Upstream product

• 3278-35-1 S-(ethoxycarbonyl) O-ethyl dithiocarbonate 
• 109-73-9 N-butylamine 
• 74-88-4 methyl iodide 
• 136490-79-4 S-trimethylsilyl O-ethyldithiocarbonate 
• 140-89-6 potassium ethyl xanthogenate 

Downstream Products

• 625-57-0 O-ethyl thiocarbamate 
• 17996-38-2 N,N-dimethyl ethyl thiocarbamate 
• 868-84-8 S,S-dimethyl dithiocarbonate 
• 623-80-3 S,S-diethyl dithiocarbonate 
• 10596-55-1 S-Ethyl S'-methyl dithiocarbonate 
• 4468-82-0 O-ethyl hydrazinothioformate 
• 123457-63-6 1-ethoxy-4-dimethylaminopyridinium S-methyldithiocarbonate 
• 110921-56-7 2-hydroxycyclohex-1-ene-1-carbothioate de O-ethyle 
• 927-01-5 N-ethoxythiocarbonyl-N',N'-dimethylhydrazine 
• 62157-44-2 N-Aethoxythiocarbonyldiphenylsulfimid 
• 74-93-1 methylthiol 
• 74-85-1 ethene 
• 16516-19-1 O-ethyl 3-oxo-3-phenylpropanethioate 
• 53146-48-8 5-tert-butyl-1,3-benzoxazole-2(3H)-thione 

Relevant academic research and scientific papers

PYROTHIOCARBONATES V. SYNTHESIS AND SOME REACTIONS OF S-TRIMETHYLSILYL O-ALKYLDITHIOCARBONATES

Non-reported S-trimethylsilyl-O-alkyldithiocarbonates (2) are prepared by reaction of O,O-dialkyltrithiodicarbonates with N-methyl-N-trimethylsilylaniline in 87-96percent yield.These air-sensitive liquids which are separated from accompanying phenyl methyl alkylcarbamothioates by fractional distillation.The reaction of 2 with acetyl chloride gives the unsymmetrical dithioanhydrides S-acetyl O-alkyldithiocarbonates in 93-97percent yield.With the less powerfull electrophilic reagent, iodomethane, S-trimethylsilyl O-ethyldithiocarbonate (2a) forms S-methyl O-ethyldithiocarbonate in 30percent yield.When a chloroform solution of 2a is stirred with water the unstable compound O-ethyldithiocarbonic acid is obtained. Key words: Masked O-alkyldithiocarbonic acids; O,O-dialkyltrithiodicarbonates; S-acetyl O-alkyl-dithiocarbonates.

PYROTHIOCARBONATES I. AMINOLYSIS OF S-(ETHOXYCARBONYL) O-ETHYL DITHIOCARBONATE

The reaction of S-(ethoxycarbonyl) O-ethyl dithiocarbonate (1) with equimolar amounts of butylamine, benzylamine, diethylamine and piperidine in ethanol solution at 0 deg C is reported.The mole ratio of O-ethyl thiocarbamate (2) and O-ethyl carbamate (3) formed as main products is larger than unity during all the reaction.Bis(ethoxythiocarbonyl) sulfide (4) and bis(ethoxycarbonyl) sulfide (5) are also produced and their formation is explained in terms of the reaction of 1 with EtOCS2- and EtOCOS-, respectively, which are the leaving groups in the aminolysis of 1.Reactions 4 -> 2 and 5 -> 3 also take place.When 50percent of 1 has been consumed compound 4 is not detected and compound 5 is found at very low concentration, indicating that generation of 4 and 5 occurs mainly after aminolysis of 1.The fact that the ratio of 2 : 3 is larger than unity in this aminolysis step, and that S-methyl O-ethyldithiocarbonate is aminolyzed more readily than S-methyl O-ethylmonothiocarbonate under the same conditions as the aminolysis of 1, suggests that the thiocarbonyl group of 1 is more reactive than the carbonyl group.