22020-90-2

Basic information

• Product Name: Thiirane, 2,3-diphenyl-, 1,1-dioxide
• CAS NO: 22020-90-2
• Molecular Formula: C14H12O2S
• Molecular Weight: 244.314
• Mol File: 22020-90-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Thiirane, 2,3-diphenyl-, 1,1-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: Thiirane, 2,3-diphenyl-, 1,1-dioxide(22020-90-2)
• EPA Substance Registry System: Thiirane, 2,3-diphenyl-, 1,1-dioxide(22020-90-2)

Safety Data

• Hazardous Substances Data: 22020-90-2(Hazardous Substances Data)

Upstream product

• 3372-81-4 trans-stilbene sulfide 
• 908094-04-2 phenyldiazomethane 
• 1939-99-7 benzenesulfonyl chloride 

Downstream Products

• 588-59-0 stilbene 

Relevant articles and documents

Efficient synthesis of episulfones and of SO2 with any variation of oxygen isotopes using HOF·CH3CN

Episulfones are quite unstable and difficult to make compounds. HOF·CH3CN, a powerful oxygen transfer agent operating under very mild conditions, was successfully employed in converting episulfides to episulfones. Unlike other oxidizing agents,

trans-2,3-Di-tert-butylthiirane 1,1-Dioxide and 2,5-Di-tert-butyl-2,5-dihydro-1,3,4-thiadiazole 1,1-Dioxides from tert-Butyldiazomethane and Sulfur Dioxide. Solvent Effects and Mechanisms of the Staudinger-Pfenninger-Reaction

When allowed to react with sulfur dioxide tert-butyldiazomethane formed not only trans-di-tert-butylthiirane 1,1-dioxide (3) but also the diastereomeric 2,5-dihydro-1,3,4-thiadiazole 1,1-dioxides 7e which under base-catalysis rearranged to the 2,3-dihydro-1,3,4-thiadiazole 1,1-dioxide 11.The structures were deduced from IR, UV, and 1H-NMR-spectra, and from the products obtained after loss sulfur dioxide.Whereas increase of the solvent polarity favoured 3 over 7e, the diastereomer ratio cis-7e/trans-7e remained virtually unaffected.The ratio of thiirane 1,1-dioxide 3 to dihydrothiadiazole 1,1-dioxides did not depend on whether the intermediate tert-butylsulfene 6e had been generated from 5e and sulfur dioxide or from 2,2-dimethylpropane sulfonylchloride (14) and triethylamine.In contrast to reports in the literature, the reaction of the phenyldiazoalkanes 5f and 5h with sulfur dioxide afforded cis/trans ratios of the thiirane 1,1-dioxides 9f and 9h, respectively, which were only slightly influenced by the solvent.Apparently, the dihydrothiadiazole 1,1-dioxides 7 and hence their decomposition products, the azines 8 (as far as these do not arise from the direct decomposition of the diazo compounds), are the result of a cycloaddition between the diazoalkane 5 and the sulfene 6.In contrast, the thiirane 1,1-dioxides 9 seem to originate via the zwitterions 20 the formation of which is favoured over the cycloaddition by solvents of high polarity, by the presence of aryl substituents at the sulfene, as well as by the lack of alkyl groups.The dichotomy in the behaviour of sulfenes towards diazoalkanes can be traced back to the existence of two low-lying sulfene MO's, only one of which exhibits ?-symmetry.