REACTION OF α-BENZENESULFONYLPHENYLACETIC ACID WITH ALKYL HALIDES. DECARBOXYLATIVE ALKYLATION VS. DECARBOXYLATIVE PROTONATION

The reaction of α-benzenesulfonylphenylacetic acid with some alkyl halides, using as base NaH in DMSO, leads to decarboxylative protonation to give benzylphenylsulfone. Decarboxylative alkylation occurs only when CO2 is expelled by flushing with nitrogen. The mechanism of the decarboxylative protonation is investigated.