84224-65-7

Basic information

• Product Name: Benzenesulfenyl Triflate
• Synonyms: Benzenesulfenyl Triflate
• CAS NO: 84224-65-7
• Molecular Formula: C₇H₅F₃O₃S₂
• Molecular Weight: 258.2380096
• Mol File: 84224-65-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzenesulfenyl Triflate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfenyl Triflate(84224-65-7)
• EPA Substance Registry System: Benzenesulfenyl Triflate(84224-65-7)

Safety Data

• Hazardous Substances Data: 84224-65-7(Hazardous Substances Data)

Upstream product

• 2923-28-6 silver trifluoromethanesulfonate 
• 931-59-9 benzenesulfenyl chloride 

Downstream Products

• 314740-77-7 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl triflate 
• 59980-96-0 Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 

Relevant articles and documents

Highly diastereoselective α-mannopyranosylation in the absence of participating protecting groups

S-Phenyl 2,6-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)- 1- thia-α-D-mannopyranoside and its sulfoxide, following activation at -78 °C with benzenesulfenyl triflate or trifiic anhydride, respectively, provide the corresponding α-mannosyl triflate as demonstrated by NMR spectroscopy. On addition of an acceptor alcohol α-mannosides are then formed. Similarly, S- phenyl 2,3-O-carbonyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside and ethyl 3-O-benzoyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-1-thia-α-D- mannopyranoside both provide α-mannosides on activation with benzenesulfenyl triflate followed by addition of an alcohol. These results stand in direct contrast to the highly β-selective couplings of comparable glycosylations with 2,3-di-O-benzyl-4,6-O-benzylidene protected mannosyl donors and draw attention to the subtle interplay of reactivity and structure in carbohydrate chemistry.

Synthesis and Reactions of Sulfenic Trifluoromethanesulfonic Anhydrides

Sulfenyl halogenides 1 and 4 react with silver trifluoromethanesulfonate (2) to give aryl 3 and alkylsulfenic trifluoromethanesulfonic anhydrides 5, resp., in good yields; 3 and 5 could not be isolated because of their instability. 1H NMR spectroscopic data of 5a, b, each in dichloromethane and nitromethane, resp., are indicative of a dissoziation to adducts of alkylsulfenylium ions and the solvent.Whereas 3 do not react with aromatic compounds, addition products with diphenylacetylene, arylsulfenylvinyl trifluoromethanesulfonates 11, are formed smoothly, which under the reaction conditions immediately cyclize to give benzothiophenes 10 in excellent yields.