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Synthesis, 13C NMR, and UV spectroscopic study of 13C-labeled nitrile N-oxide

Authors :
Shigeki Kuroki
Young-Gi Lee
Toshikazu Takata
Yasuhito Koyama
Source :
Tetrahedron Letters. 56:7038-7042
Publication Year :
2015
Publisher :
Elsevier BV, 2015.

Abstract

13 C-labeled nitrile N -oxides ( 13 CNOs) were prepared to investigate the structural characteristics of nitrile N -oxide in solution. In the 13 C NMR spectra at room temperature, 13 C signals of 13 CNOs appeared at 35–38 ppm. The chemical shift of adjacent aromatic carbon C a to 13 CNO was remarkably upfield-shifted to indicate a positive mesomery effect of CNO. The 13 C NMR signal appeared as a triplet that originated from the scalar coupling of the adjacent 14 N nucleus, while it fused into a singlet as the temperature decreased. The UV spectra of 13 CNOs also indicated the temperature-dependent dynamic character of CNO.

Details

ISSN :
00404039
Volume :
56
Database :
OpenAIRE
Journal :
Tetrahedron Letters
Accession number :
edsair.doi...........9217f6a6a8fed5aeacabfa26b3e07941