73558-54-0

Basic information

• Product Name: (E)-1,2-Diphenylvinylsulfonyl fluoride
• Synonyms: (E)-1,2-Diphenylvinylsulfonyl fluoride
• CAS NO: 73558-54-0
• Molecular Weight: 262.305
• Mol File: 73558-54-0.mol

Chemical Properties

• CAS DataBase Reference: (E)-1,2-Diphenylvinylsulfonyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1,2-Diphenylvinylsulfonyl fluoride(73558-54-0)
• EPA Substance Registry System: (E)-1,2-Diphenylvinylsulfonyl fluoride(73558-54-0)

Safety Data

• Hazardous Substances Data: 73558-54-0(Hazardous Substances Data)

Upstream product

• 588-59-0 stilbene 
• 56437-49-1 (E)-1,2-Diphenylvinylsulfonyl chloride 
• 5162-99-2 2,3-Diphenylthiirene 1,1-dioxide 

Relevant articles and documents

Radical Fluorosulfonylation: Accessing Alkenyl Sulfonyl Fluorides from Alkenes

Sulfonyl fluorides have widespread applications in many fields. In particular, their unique biological activity has drawn considerable research interest in the context of chemical biology and drug discovery in the past years. Therefore, new and efficient methods for the synthesis of sulfonyl fluorides are highly in demand. In contrast to extensive studies on FSO2+-type reagents, a radical fluorosulfonylation reaction with a fluorosulfonyl radical (FSO2.) remains elusive so far, probably owing to its instability and difficulty in generation. Herein, the development of the first radical fluorosulfonylation of alkenes based on FSO2 radicals generated under photoredox conditions is reported. This radical approach provides a new and general access to alkenyl sulfonyl fluorides, including structures that would otherwise be challenging to synthesize with previously established cross-coupling methods. Moreover, extension to the late-stage fluorosulfonylation of natural products is also demonstrated.

Reactions of 2,3-Diphenylthiirene 1,1-Dioxide with Nucleophiles

A series of nucleophiles was allowed to react with 2,3-diphenylthiirene 1,1-dioxide (1) in dipolar aprotic solvents to produce a variety of derivatives.Fluoride ion gave diphenylacetylene and (E)-1,2-diphenylvinylsulfonyl fluoride (2);thiophenoxide gave (E)-1,2-diphenyl-2-(thiophenoxy)vinylsulfinate which gave the corresponding methyl sulfone 5 on treatment with methyl iodide.Azide ion gave a variety of products including diphenylvinyl azides 12 and 13, 2,3-diphenylazirine (14), 2,6-diphenyl-4-((E)-diphenylvinyl)-1,3,4,5-thiatriazine 1,1-dioxide (15),benzil (16), 4,5-diphenyltriazole (17), 2,4,5-triphenylimidazole (18),and (Z)-1,2-diphenyl-2-azidovinylsulfinate which gave the corresponding methyl sulfone 22 on treatment with methyl iodide.The diphenylvinyl group was removed from the new heterocycle 15 by ozonolysis followed by mild base hydrolysis to yield the thiatriazine 1,1-dioxide 20.Compound 20 undergoes thermolysis at 40 deg C to give stilbenes,and 20 also undergoes a facile base-catalyzed extrusion of sulfur dioxide to give imidazole 18.