132283-38-6

Basic information

• Product Name: methyl 2-(p-methoxyphenyl)-6-methyl-1,4,3-oxathiazine-5-carboxylate
• Synonyms: methyl 2-(p-methoxyphenyl)-6-methyl-1,4,3-oxathiazine-5-carboxylate
• CAS NO: 132283-38-6
• Molecular Weight: 279.317
• Mol File: 132283-38-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl 2-(p-methoxyphenyl)-6-methyl-1,4,3-oxathiazine-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-(p-methoxyphenyl)-6-methyl-1,4,3-oxathiazine-5-carboxylate(132283-38-6)
• EPA Substance Registry System: methyl 2-(p-methoxyphenyl)-6-methyl-1,4,3-oxathiazine-5-carboxylate(132283-38-6)

Safety Data

• Hazardous Substances Data: 132283-38-6(Hazardous Substances Data)

Upstream product

• 24762-04-7 2-Diazo-3-oxo-butyric acid methyl ester 
• 52533-09-2 5-(4-methoxyphenyl)-[1,3,4]oxathiazol-2-one 

Relevant articles and documents

Rhodium-catalysed Reaction of Methyl Diazoacetoacetate with 5-(p-Methoxyphenyl)-1,3,4-oxathiazol-2-one; Isolation and Crystal Structure of Methyl 2-(p-Methoxyphenyl)-6-methyl-1,4,3-oxathiazine-5-carboxylate

The rhodium(II)-catalysed reaction of methyl diazoacetoacetate with 5-(p-methoxyphenyl)-1,3,4-oxathiazol-2-one afforded p-methoxybenzonitrile, the title 1,4,3-oxathiazine (17), dithietane (9), and thiirane (10).The structure of the oxathiazine was confirmed by X-ray crystallography; the heterocyclic ring is folded (20 deg) along the S-O axis.A mechanism is proposed involving initial formation of a sulphonium ylide (23) followed by ring expansion with decarboxylation.The oxathiazine is thermally unstable undergoing retro-Diels Alder fragmentation to p-methoxybenzonitrile and dithietane and thiirane products derived from methyl α-thioxoacetoacetate.The corresponding reaction with dimethyl diazomalonate afforded p-methoxybenzonitrile and oligomers of dimethyl α-thioxomalonate; an intermediate oxathiazine was not detected.