NOVEL LIGANDS FOR METAL CATALYSED CHEMICAL WARFARE DECONTAMINATION: SYNTHESIS BIS-(6-HYDROXYIMINOMETHYL-2-PYRIDYL)METHANE

Authors
  1. Lloyd, B.
Corporate Authors
Defence Research Establishment Suffield, Ralston ALTA (CAN);Medicine Hat Coll, Medicine Hat ALTA (CAN)
Abstract
The synthesis of bis-(6-hydroxyiminomethyl-2-pyridyl)methane was not achieved via the proposed synthetic route. The dipyridyl derivatives bis-(6-bromo-2-pyridyl)acetonitrile and bis-(6-halo-2-pyridyl) methane, (the term halo is used to represent a mixture of the three possible dibromo, 7a, bromochloro, 7b, and dichloro, 7c, adducts) were synthesized and characterized by 1H NMR and GC/MS. The spectra of bis-(6-bromo-2-pyridyl)acetonitrile revealed the presence of two tautomers, one processing a bifurcated hydrogen bond, N-H...N group, 6a, the other a bridging CHC=N group, 6b. This tautomerization process and the spectral properties of the two tautomers were investigated; the second order 1H NMR spectrum of 6a was successfully simulated as an ABCD spin system. The attempt to generate the required precursor bis-(6-bromo-2-pyridyl)methane through a decarbonylation reaction of the hydrolyzed product of 6 was complicated by the unreported nucleophilic substitution of the bromo-functional groups with chloride from the reagent HCl. The extent of substitution for two different reaction durations was determined. Reactions of bis-(6-halo-2-pyridyl)methane with both N,N-dimethylformamide and ethyl formate under a variety of conditions was studied. Based upon this work an alternative synthetic route to generate the target molecule was determined and proposed.
Report Number
DRES-CR-93-07 — Contract Report
Date of publication
01 Dec 1992
Number of Pages
20
DSTKIM No
93-01480
CANDIS No
129339
Format(s):
Hardcopy;Originator's fiche received by DSIS

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