Abstract

The kinetics of the reactions of secondary alicyclic amines with bis(4-nitrophenyl) carbonate (1), S-(4-nitrophenyl) O-(4-nitrophenyl) thiocarbonate (2) and S-(4-nitrophenyl) O-(4-nitrophenyl) dithiocarbonate (3) were studied at 25.0 °C. The reactions of 1 were studied in water and those of 2 and 3 in 44 wt% ethanol–water. These reactions are concerted. The HPLC analyses of the reactions of 2 and 3 with morpholine show that both 4-nitrophenoxide and 4-nitrobenzenethiolate ions are the nucleofuges.