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Configurational assignment by 13C NMR of stereoisomeric epoxyspirocyclohexanes derived from 4-tert-butylcyclohexanone

✍ Scribed by T. Bottin-Strzalko; M. C. Roux-Schmitt

Publisher
John Wiley and Sons
Year
1980
Tongue
English
Weight
159 KB
Volume
14
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The equatorial or axial configurational assignment of stereisomeric epoxyspirocyclohexanes, derived from the reaction of 4‐tert‐butylcyclohexanone with the anion of 2‐chloropropionitrile, has been determined by comparing the ^13^C chemical shifts of these compounds with those of the parent compounds, of known configuration, and resulting from the condensation of the anion of chloracetonitrile with 4‐tert‐butylcyclohexanone. A high field shift is observed for the cyclohexane ring carbons on going from the equatorial to the axial epoxide.

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