ChemInform Abstract: APPLICATION OF THE MESITYL GROUP AS AN NMR PROBE FOR THE DETERMINATION OF ANISOTROPY EFFECTS DUE TO RING CURRENTS, I. PROTON NMR SPECTRA OF MONOSUBSTITUTED DERIVATIVES OF MESITYLENE

1976 ◽  
Vol 7 (19) ◽  
pp. no-no
Author(s):  
GUENTER HAEFELINGER ◽  
FRITZ HACK ◽  
GERLINDE WESTERMAYER
Keyword(s):  
Nmr Spectra ◽  
Proton Nmr ◽  
Ring Currents ◽  
Derivatives Of

scholarly journals N-(tert-Butyldimethylsilyl)imidazole and related heterocycles: 13C nuclear magnetic resonance study and reaction with dimethylsulfoxide

1980 ◽  
Vol 58 (1) ◽  
pp. 60-64 ◽  
Author(s):  
Alexander F. Janzen ◽  
Gerald N. Lypka ◽  
Roderick E. Wasylishen
Keyword(s):  
Mass Spectrometry ◽  
Elemental Analysis ◽  
Nmr Spectra ◽  
Elevated Temperatures ◽  
Proton Nmr ◽  
Nuclear Magnetic Resonance Study ◽  
Magnetic Resonance Study ◽  
13C Nuclear Magnetic Resonance ◽  
Methyl Derivatives ◽  
Derivatives Of

N-tert-Butyldimethylsilyl derivatives of imidazole, 2-methylimidazole, 4-methylimidazole, benzimidazole, pyrazole, 1,2,4-triazole, and benzotriazole were prepared from tert-butyldimethylsilyl chloride and the corresponding heterocyclic compound. The products were identified by carbon and proton nmr, mass spectrometry, and elemental analysis. The carbon nmr spectra confirmed the absence of intermolecular silyl exchange at ambient temperature. Silyl exchange did occur at elevated temperatures, 130–160 °C.Reaction of N-tert-butyldimethylsilyl or N-trimethylsilyl heterocycles with dimethylsulfoxide gave N-(methylthio)methyl derivatives of imidazole, 2-methylimidazole, 4-methylimidazole, benzimidazole, pyrazole, and 1,2,4-triazole. The products were characterized by carbon and proton nmr, mass spectrometry, and elemental analysis. A mechanism involving a Pummerer rearrangement is proposed to account for the results.

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