Sulfamides and Sulfonamides as Polar Aprotic Solvents

Article abstract of DOI:10.1021/jo00380a001

Five tetraalkylsulfamides, one N,N-dialkylsulfonamide, two sulfurous diamides, and one sulfinamide were investigated for potential use as polar aprotic solvents that would be compatible with strongly basic and nucleophilic reagents.The values of Taft β and ?^* measured for these compounds indicated that all possess significant polar aprotic solvent character.Their stabilities toward ethylmagnesium bromide, diethylzinc, methyllithium, and butyllithium were determined.Tetraethylsulfamide (Et2NSO2NEt2) and N,N-diethyltrimethylmethanesulfonamide (Me3CSO2NEt2) were the most stable of the solvents, showing no evidence of decomposition with the magnesium or zinc compounds and an appreciable lifetime with methyllithium.