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Synthesis and HPLC resolution of isomers of novel phosphorus fluorinated 2,4,6-trimethylphenylazo pyridines
Zineb Hacini (1,*)
, Lakhdar Sekhri (2) (1) Department of Chemistry, University of Hadj Lakhdar, Batna, 05000, Algeria
(2) Department of Chemistry, University of Kasdi Merbah, Ouargla, 30000, Algeria
(*) Corresponding Author
Received: 05 Mar 2016, Accepted: 17 Apr 2016, Published: 30 Jun 2016
Abstract
New compounds of phosphorus fluorinated 2,4,6-trimethylphenylazo pyridines (4a-c) have been synthesized in high yields via adding n-butyl lithium in hexane to a stirred solution of methyldiphenylphosphine oxide in dry THF at 0 °C, then cooled to around -78 °C, treated with azo-pyridines(2a-c) and then allowed to warm at room temperature over 2 h. The isomers of (E)-((5-chloro-3,6-difuoro-4-(mesityldiazenyl)pyridin-2-yl)methyl)diphenyl phosphine oxide (4b) and (E)-((3,6-difuoro-4-(mesityldiazenyl)5-methoxypyridin-2-yl)methyl)diphenyl phosphine oxide (4c) can be separated on analytical HPLC: Chiralcel OD-H column, hexane:2-PrOH, (9:1, v:v) mobile phase, flow-rate, 1.0 mL/min, 25 °C, λ = 254 nm and polarimetric detection, 20 µL injection volume. The resolution of this isomers were 2.12, 1.84, respectively.
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DOI: 10.5155/eurjchem.7.2.225-229.1423
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DOI Link: https://doi.org/10.5155/eurjchem.7.2.225-229.1423
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