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Kinetics of dehydrohalogenation of N-chloro-3-azabicyclo[3,3,0]octane in alkaline medium. NMR and ES/MS evidence of the dimerization of 3-azabicyclo[3,3,0]oct-2-ene

✍ Scribed by M. Elkhatib; L. Peyrot; J. P. Scharff; H. Delalu

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
199 KB
Volume
30
Category
Article
ISSN
0538-8066

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✦ Synopsis

The formation of 3-azabicyclo [3,3,0]oct-2-ene in the course of the synthesis of 3,0]octane using the Raschig process results from the following two consecutive reactions: chlorine transfer between the monochloramine and the 3-azabicyclo[3,3,0]octane followed by a dehydrohalogenation of the substituted haloamine. The kinetics of the reaction were studied by HPLC and UV as a function of temperature (15 to 44ЊC), and the concentrations of NaOH (0.1 to ) and the chlorinated derivative (1 to ). Ϫ3 1 M 4 ϫ 10 M The reaction is bimolecular ( ; ; and Ϫ6 Ϫ1 Ϫ1 0 # Ϫ 1 0 # k ϭ 103 ϫ 10 M s ⌬H ϭ 89 kJ mol ⌬S ϭ ) and has an E2 mechanism. The spectral data of 3-azabicyclo[3,3,0]oct-2-Ϫ1 Ϫ1

Ϫ33.6 J mol K ene were determined. IR, NMR, and ES/MS analysis show dimerization of the water-soluble monomer into a white insoluble dimer.

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