FORMATION OF SULFINATE ESTERS IN THE SYNTHESIS OF TRIFLATES

On standard treatment of sterically congested alcohols and phenols wit h triflic anhydride in the presence of amines, trifluoromethanesulfiny l esters were unexpectedly found. Depending on the reaction conditions and the structures of both hydroxy compound and base, esterified prod ucts (yields <5% to 99%) containing 0% to 89% (!) of sulfinates were o btained. The mechanisms of these reactions are discussed. The results of the present study indicate how to avoid unwanted sulfinate formatio n in triflate synthesis. Copyright (C) 1996 Elsevier Science Ltd