Excellent correlation between substituent constants and pyridinium N-methyl chemical shifts

Tetrahedron Letters

Volumn 50, Issue 35, 2009, Pages 5018-5020

  Huang, Sha ^a   Wong, Jesse C S ^a   Leung, Adam K C ^a   Chan, Yee Man ^a   Wong, Lili ^a   Fernendez, Myrien R ^a   Miller, Amanda K ^a   Wu, Weiming ^a  

^a SAN FRANCISCO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDOXINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 67650078942     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.081     Document Type: Article

References (11)

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5. Ehrensen S., Brownlee R.T.C., and Taft R.W. Prog. Phys. Org. Chem. 10 (1973) 1-80
6. Wong F.M., Capule C.C., Chen D.X., Gronert S., and Wu W. Org. Lett. 10 (2008) 2757-2760
7. Typical experimental procedures: Pyridine (1 g) was dissolved in 5 mL anhydrous ethyl ether in a pressure tube. Methyl iodide (3 g) was added to the solution and the mixture was stirred overnight at room temperature. The resulting solid was filtered, washed with anhydrous ethyl ether, and dried to give N-methylpyridinium iodide as a white solid. In cases when the pyridine derivatives are not soluble enough in ether, ethyl acetate was used as the reaction solvent. All chemicals are commercially available and are used without further purification. NMR spectra were obtained with either QE 300 or Bruker 500 instruments. All chemical sifts are referenced to sodium 3-trimethylsilylpropionate at 0.00 ppm.
8. Chen D.X., Ho C.M., Wu Q.Y.R., Wu P.R., Wong F.M., and Wu W. Tetrahedron Lett. 49 (2008) 4147-4148
9. 1H NMR, respectively.
10. Taft R.W., Price E., Fox I.R., Lewis I.C., Anderson K.K., and Davis G.T. J. Am. Chem. Soc. 85 (1963) 709-724
11. 13C NMR, respectively.