Activated Sterically Strained C=N Bond in N-Substituted p-Quinone Mono- and Diimines: XVI. Structural Characteristics

Activated Sterically Strained C=N Bond in N-Substituted p-Quinone Mono- and Diimines: XVI.... N-Substituted 1,4-quinone imines with an activated sterically hindered C=N bond characteristically react with nucleophiles via 1,2-addition to that bond with formation of quinolide compounds. The C=N–X bond angle in these quinone imines ranges from 130 to 145°, the upper limit being defined by their thermodynamic stability. According to the X-ray diffraction data, the real C=N–X can be smaller than 130°C, but in this case considerable deviations of the nitrogen atom and substituent attached thereto from the mean-square plane of the quinoid ring and twisting of the C=N bond are observed. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Russian Journal of Organic Chemistry Springer Journals

Activated Sterically Strained C=N Bond in N-Substituted p-Quinone Mono- and Diimines: XVI. Structural Characteristics

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Publisher
Pleiades Publishing
Copyright
Copyright © 2018 by Pleiades Publishing, Ltd.
Subject
Chemistry; Organic Chemistry
ISSN
1070-4280
eISSN
1608-3393
D.O.I.
10.1134/S1070428018010050
Publisher site
See Article on Publisher Site

Abstract

N-Substituted 1,4-quinone imines with an activated sterically hindered C=N bond characteristically react with nucleophiles via 1,2-addition to that bond with formation of quinolide compounds. The C=N–X bond angle in these quinone imines ranges from 130 to 145°, the upper limit being defined by their thermodynamic stability. According to the X-ray diffraction data, the real C=N–X can be smaller than 130°C, but in this case considerable deviations of the nitrogen atom and substituent attached thereto from the mean-square plane of the quinoid ring and twisting of the C=N bond are observed.

Journal

Russian Journal of Organic ChemistrySpringer Journals

Published: Mar 13, 2018

References

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