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Sulfonium salts [R 2 S-CH 2 -OTf] +  OTf -  1a,b are synthetically versatile 1,1-biselectrophiles featuring the sulfonio- and triflato-substituents as leaving groups of differential nucleofugic power. Reactions with a number of neutral nucleophiles |Nu yield a series of novel sulfoniom ethylated onium salts [R 2 S-CH 2 -Nu] 2+  2OTf -  2 - 8 under very mild conditions. Structures of salts 2a, 5a and 6b were confirm ed by X -ray analysis. With certain N -hetarenes exchange of both nucleofuges in la was achieved, yielding the symmetrical 1,1-bisonium salts 9 and 10. With pyridine(derivatives) selective substitution of the sulfoniofunction in 1,1-bisonium systems 2a and 5a was also realized. These reactions represent typical examples of nucleophilic substitutions at geminally bisonio substituted Csp 3  centers, which we recently have introduced as a novel variant of S ɴ 2 reactivity.

[R 2 S-CH 2 -OTf] + OTf – as a Reagent with an Optionally Mono-or Biselectrophilic Csp 3 Center