Sulfonium, Ethenyldiphenyl-, 1,1,1-Trifluoromethanesulfonate

[247129-88-0] C15H13F3O3S2 (MW 362.39) InChI = 1S/C14H13S.CHF3O3S/c1-2-15(13-9-5-3-6-10-13)14-11-7-4-8-12-14;2-1(3,4)8(5,6)7/h2-12H,1H2;(H,5,6,7)/q+1;/p-1 InChIKey = OKDGDBRZMJNKLV-UHFFFAOYSA-M (good Michael acceptor, soft electrophile, used for epoxidation, aziridination, and other annulation reactions) Alternate Name: diphenylvinylsulfonium triflate. Physical Data: free-flowing pale yellow or light brown/gray oil. Solubility: soluble in CH2Cl2, CHCl3, MeOH, EtOH, THF, DMF, MeCN, toluene, DMSO. Preparative Method: reaction of 2-bromoethyl triflate with diphenyl sulfide (eq 1) followed by treating the resulting crystalline bromoethylsulfonium triflate with base generates the diphenylvinylsulfonium triflate (eq 2).1 Bromoethylsulfonium triflate is also commercially available. Protocols that involve the generation of diphenylvinylsulfonium triflate in situ from bromoethylsulfonium triflate have also been described (see below). (1) (2) Handling, Storage, and Precautions: is stable at room temperature, but it is slightly hydroscopic and should be stored appropriately (e.g., under nitrogen/argon in a container sealed with parafilm); sometimes a dark green/black colored diphenylvinylsulfonium triflate is obtained1 (this was observed if a bottle of ‘old’ triflic anhydride was used in the synthesis of 2-bromoethyl triflate) but it could be used in much of the chemistry described below without detriment. Its toxicity has not been studied; however, as it is a potent alkylating agent, it should be manipulated with care (use of DMSO as solvent should be avoided). Skin/eye contact should be avoided.