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C. Darwich, M. Elkhatib, G. Steinhauser, H. Delalu:
"Chlorine-Atom Transfer Reactions between Chloramine (0Chloramide) and Piperidine: Kinetic Reactivity and Characterization in a Raschig Medium";
Helvetica Chimica Acta, 92 (2009), 98 - 111.

The kinetics of the Cl-transfer reaction between chloramine (1) and piperdine (2) in a Raschig medium (8< pH <9) was studied at various temperatures, with variable concentrations of the two reactants. The influence of the pH on the interaction of 1 and 2 was examined at a pH ranging between 8,25 and 12,89. The Cl-transfer reaction resulted in the formation of 1-chloropiperidine (3), which, in the presence of NaOH, underwent a dehydrohalogenation leading to an endocyclic imine derivate: 2,3,4,5-tetrahydropyridine (4). The kinetics of the dehydrohalogenation was also studied at different temperatures, with variable concentrations of 3 and NaOH. Kinetic and thermodynamic parameters were determined for the Cl-transfer and dehydrohalogenation reactions. Both 3 and 4 were prepared according to efficient synthetic routes; they were isolated, purified, and characterized by elemental analysis, IR, ¹H- and ¹³C-NMR, and MS. Their thermal stabilities were evaluated by differential scanning calorimetry (DSC), and their absorption coefficients at various wavelengths were determined experimentally by UV spectrophotometry.

http://publik.tuwien.ac.at/files/PubDat_173701.pdf