Anomeric Effect of the Nitrogen Atom in the Isocyano and Urea Groups

Y Ichikawa, H Watanabe, H Kotsuki…

Index: Ichikawa, Yoshiyasu; Watanabe, Hitomi; Kotsuki, Hiyoshizo; Nakano, Keiji European Journal of Organic Chemistry, 2010 , # 33 p. 6331 - 6337

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Citation Number: 7

Abstract

Abstract The anomeric effect associated with the nitrogen atom in the isocyano group was investigated by using 1 H NMR spectroscopic analysis of an anomeric pair of xylopyranosyl isocyanides 8 and 7. We found that β-anomer 7 prefers to exist in the 1 C 4 conformation in which the nitrogen atom in the isocyano group adopts an axial orientation. This observation, coupled with the results of X-ray crystallographic analysis establishes that the nitrogen ...