Chlorine-Atom Transfer Reactions between Chloramine (=Chloramide) and Piperidine: Kinetic Reactivity and Characterization in a Raschig Medium

✍ Scribed by Chaza Darwich; Mazen Elkhatib; Georg Steinhauser; Henri Delalu

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: German
• Weight: 343 KB
• Volume: 92
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200800223

✦ Synopsis

Abstract

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The kinetics of the Cl‐transfer reaction between chloramine (1) and piperidine (2) in a Raschig medium (81 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 derivative: 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, ^1^H‐ and ^13^C‐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.