59291-73-5

Upstream product

• 62157-41-9 N-(4-methoxy-thiobenzoyl)-S,S-diphenyl-sulfimide 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 73501-02-7 5-(p-methoxyphenyl)-2-trichloromethyl-1,3,4-oxathiazole 
• 73501-03-8 5-(p-methoxyphenyl)-2,2-bis(trichloromethyl)-1,3,4-oxathiazole 
• 73501-04-9 5-(p-methoxyphenyl)-2-phenyl-2-trifluoromethyl-1,3,4-oxathiazole 
• 15965-45-4 3-(4-methoxy-phenyl)-[1,4,2]dithiazol-5-one 
• 99315-71-6 dichloromethylene-5-(p-methoxyphenyl)-1,3,4-oxathiazole 
• 104478-87-7 5-(p-chlorophenyl)-3-(p-methoxyphenyl)-4-phenyl-4,5-dihydro-1,2,4-thiadiazole 
• 2362-64-3 p-methoxythiobenzamide 
• 15965-42-1 3-(p-methoxyphenyl)-1,4,2-dithiazole-5-thione 
• 5874-09-9 methyl (4-methoxyphenyl)carbodithioate 

Relevant academic research and scientific papers

Nitrile Sulphides. Part 5. 1,3-Dipolar Cycloaddition of p-Methoxybenzonitrile Sulphide to Imines and Crystal Structure of One of the Resulting 4,5-Dihydro-1,2,4-thiadiazoles

p-Methoxybenzonitrile sulphide, generated by thermal fragmentation of the corresponding 1,3,4-oxathiazol-2-one, undergoes 1,3-dipolar cycloaddition to imines forming 4,5-dihydro-1,2,4-thiadiazoles.X-ray crystal structure analysis shows that the heterocyclic ring is non-planar with a fold of 30 deg about the S(1) - N(4) vector.

Nitrile Sulphides. Part 3. Thermal Fragmentation of 1,3,4-Oxathiazoles: Formation of Nitrile Sulphides in a Retro-1,3-dipolar Cycloaddition Reaction

On thermolysis at ca. 160 gradC 1,3,4-oxathiazoles undergo retro-1,3-dipolar cycloaddition forming nitrile sulphides and carbonyl-containing fragments.The nitrile sulphides either decompose to sulphur and nitriles or are trapped as their 1,3-dipolar cycloadducts in the presence of dipolarophiles (dimethyl acetylenedicarboxylate, ethyl cyanoformate, benzonitrile, ethyl propiolate).Similar ratios (1.32, l.34, 1.33, 1.31) of 4- and 5-ethoxycarbonyl-3-(p-methoxyphenyl)isothiazole obtained from four sources of p-methoxybenzonitrile sulphide with ethyl propriolate provide strong evidence for product formation from a discrete intermediate nitrile sulphide rather than via direct interaction of precursor with dipolarophile. 2-Dichloromethylene-1,3,4-oxathiazoles, prepared by dehydrochlorination of 2-trichloromethyloxathiazoles, prepared by dehydrochlorination of 2-trichlorometyloxathiazoles, likewise fragment to nitrile sulphides, but attempts to trap dichloroketene were unsuccessful.

THE THERMAL FRAGMENTATION OF 1,3,4-DITHIAZOL-2-ONES

Thermal expulsion of carbon oxysulphide from 1,3,4-dithiazol-2-ones in the presence of DMAD affords nitrile sulphide-derived dimethyl isothiazole-4,5-dicarboxylates.

Nitrile Sulphide Formation from the Thermal Fragmentation of 1,3,4-Oxathiazoles: a Retro-1,3-dipolar Cycloaddition

1,3,4-Oxathiazoles, on thermolysis, undergo retro-1,3-dipolar cycloaddition to afford carbonyl compounds and nitrile sulphides, which may be trapped by cycloaddition with alkynes and nitriles.