192320-25-5Relevant academic research and scientific papers
Chemoselective substitution in 4-toluenesulfonamides and carbamates by di-tert-butyl dicarbonate in the presence of 4-dimethylaminopyridine
Grehn, Leif,Ragnarsson, Ulf
, p. 627 - 630 (2007/10/03)
Three novel derivatives of 1,2-ethylenediamine 1, 3 and 5 with 4-toluenesulfonyl 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 reagents underwent completely selective substitution under these conditions 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 reaction sites. The products might be useful in synthesis of substituted 1,2-ethylenediamines. A similar approach might be applicable to many other diamines. Acta Chemica Scandinavica 1998.
