76162-57-7

Upstream product

• 623-47-2 propynoic acid ethyl ester 
• 52533-09-2 5-(4-methoxyphenyl)-[1,3,4]oxathiazol-2-one 
• 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 
• 73501-02-7 5-(p-methoxyphenyl)-2-trichloromethyl-1,3,4-oxathiazole 

Relevant academic research and scientific papers

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.

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.