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Title: Some interesting 1H NMR features of ortho substituted N-methoxy-N-methyl benzamides
Authors: Harikrishna, Kommidi
Balasubramaniam, Sivaraman
Rakshit, Ananya
Aidhen, Indrapal Singh
Keywords: Weinreb amide;Nuclear magnetic resonance;Benzamide;Variable temperature;Rotamers
Issue Date: Jan-2015
Publisher: NISCAIR-CSIR, India
Abstract: During synthetic efforts towards positional isomers of FTY720, using building blocks based on Weinreb amide (WA) functionality, interesting 1H NMR pattern for ortho-methyl-N-methoxy-N-methyl benzamide have been encountered. The 1H NMR spectrum has shown broad humps for N-methoxy and N-methyl units in WA functionality, whereas the spectrum for the corresponding meta-and para-isomer, displays two sharp singlets for the same units. This interesting spectral difference has been rationalized. Several ortho-substituted N-methoxy-N-methyl benzamides have been tailor-made and generality has been established. The broadening of the peaks is due to the presence of rotamers and variable temperature NMR study has unraveled that the energy barrier of two rotamers of ortho-substituted benzamides is more at room temperature, unlike para and meta substituted benzamides.
Page(s): 77-83
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.54B(01) [January 2015]

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