Supporting Data for Steric Effects of N-Alkyl Group on the Base-induced Nitrogen to Carbon Rearrangement of Orthogonally Protected N-Alkyl Arylsulphonamides

The rearrangement of a total of 56 members of 22 series of orthogonally protected N-alkyl aryl-sulphonamides of general structure 4-XC6H4SO2NR1CO2R2 [X = H, CH3, F, Cl, Br, CH3O, CN, CF3 or C(CH3)3; R1 = CH3, CH2CH3, CH2CH2CH3, CH(CH3)2 or CH2CH(CH3)2; R2 = CH3, C2H5 or C(CH3)3] when treated with lithium di-isopropylamide in tetrahydrofuran at –78 °C has been studied. The competition between directed ortho metallated rearrangement, to form 4-X-2-(R2O2C)C6H3SO2NHR1 and the production of a substituted saccharin, is strongly influenced by the size of R1 and R2, especially in the series with X = CH3.