Synthesis and Reactions of Functionalized Perfluoroalkyl Sulfones

Trifluoromethylsulfonylmethanides functionalized by a CN group

“…As we expected, a side product was isolated-the stable methane 4 [9], which is obviously an intermediate in this reaction. Salt 2 was prepared by one-pot reaction using stepwise trifluoromethylsulfonation of acetonitrile.…”

“…The solvents were pumped off, and 3 M aqueous HCl (50 mL) was added to the remaining oil. 4 was obtained as a colorless liquid, yield 40%, bp 79-81/10 mm Hg [9]. 2 was obtained as a pale yellow crystalline solid, yield 20%.…”

Trifluoromethylsulfonylmethanides functionalized by a CN group

“…It is noteworthy that carbanion 2 was isolated as the cesium salt, this being insoluble in cold water. As we expected, a side product was isolated-the stable methane 4 [9], which is obviously an intermediate in this reaction. Unfortunately, we failed to circumvent the formation of 4 by variation of the ratio of reagents.…”

Synthesis of superacidic carbon acid and its derivatives

“…Scheme 19. Self-promoting condensation reaction of Tf 2 CH 2 with paraformaldehyde Although Koshar also reported that, by using a Barrett water receiver, some aromatic aldehydes react with Tf 2 CH 2 2a in benzene under reflux conditions to give the corresponding 1,1-bis(triflyl)alkenes 26 in moderate yield [46], later Hanack noted difficulty of such condensation reactions due to very low reactivity of anionic species easily formed from (R f SO 2 ) 2 CH 2 2 [47]. Zhu reported that the condensation reaction of (R f SO 2 ) 2 CH 2 2 or 11 with aromatic aldehydes effectively proceeds in Ac 2 O as a solvent under milder conditions and the corresponding alkenes 26 are obtained in good to excellent yields (Table 3) [48].…”