CHEMOSELECTIVE SUBSTITUTION IN 4-TOLUENESULFONAMIDES AND CARBAMATES BY DI-TERT-BUTYL DICARBONATE IN THE PRESENCE OF 4-DIMETHYLAMINOPYRIDINE

Three novel derivatives of 1,2-ethylenediamine 1, 3 and 5 with 4-tolue nesulfonyl and/or carbamate moieties have been prepared and submitted to reaction with a limiting amount of di-tert-butyl dicarbonate in the presence of catalytic amounts of 4-dimethylaminopyridine. All the rea gents underwent completely selective substitution under these conditio ns and gave rise to the products 2a, 4 and 6 in 93-100% yields and the results were rationalized in terms of higher NH-acidity at the reacti on sites. The products might be useful in synthesis of substituted 1,2 -ethylenediamines. A similar approach might be applicable to many othe r diamines.