European Journal of Chemistry 2016, 7(2), 225-229. doi:10.5155/eurjchem.7.2.225-229.1423

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.


Keywords


Isomers; Synthesis; HPLC resolution; Chiralcel OD-H column; Phosphorus fluorinated; X-Ray single crystal structure

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DOI: 10.5155/eurjchem.7.2.225-229.1423

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How to cite


Hacini, Z.; Sekhri, L. Eur. J. Chem. 2016, 7(2), 225-229. doi:10.5155/eurjchem.7.2.225-229.1423
Hacini, Z.; Sekhri, L. Synthesis and HPLC resolution of isomers of novel phosphorus fluorinated 2,4,6-trimethylphenylazo pyridines. Eur. J. Chem. 2016, 7(2), 225-229. doi:10.5155/eurjchem.7.2.225-229.1423
Hacini, Z., & Sekhri, L. (2016). Synthesis and HPLC resolution of isomers of novel phosphorus fluorinated 2,4,6-trimethylphenylazo pyridines. European Journal of Chemistry, 7(2), 225-229. doi:10.5155/eurjchem.7.2.225-229.1423
Hacini, Zineb, & Lakhdar Sekhri. "Synthesis and HPLC resolution of isomers of novel phosphorus fluorinated 2,4,6-trimethylphenylazo pyridines." European Journal of Chemistry [Online], 7.2 (2016): 225-229. Web. 15 Nov. 2019
Hacini, Zineb, AND Sekhri, Lakhdar. "Synthesis and HPLC resolution of isomers of novel phosphorus fluorinated 2,4,6-trimethylphenylazo pyridines" European Journal of Chemistry [Online], Volume 7 Number 2 (30 June 2016)

DOI Link: https://doi.org/10.5155/eurjchem.7.2.225-229.1423

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