76342-95-5

Usage

Type of compound

Tetramethyl ester derivative of dithietane-2,2,4,4-tetracarboxylic acid

Structure

Unique structure with a dithietane ring and four carboxylic acid groups

Common use

Reagent in organic synthesis

Applications

Building block in the preparation of heterocyclic compounds, potential applications in pharmaceutical and material science research

Handling and storage

Requires careful handling and storage to prevent degradation and ensure stability for use in chemical reactions

InChI:InChI=1/C10H12O8S2/c1-15-5(11)9(6(12)16-2)19-10(20-9,7(13)17-3)8(14)18-4/h1-4H3

Upstream product

• 6773-29-1 dimethyl diazomalonate 
• 52533-09-2 5-(4-methoxyphenyl)-[1,3,4]oxathiazol-2-one 

Relevant academic research and scientific papers

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.