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Configurational assignment by 13 C NMR of stereoisomeric epoxyspirocyclohexanes derived from 4‐ tert ‐butylcyclohexanone
Author(s) -
BottinStrzalko T.,
RouxSchmitt M. C.
Publication year - 1980
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270140214
Subject(s) - cyclohexane , chemistry , condensation , epoxide , ion , ring (chemistry) , chemical shift , stereochemistry , computational chemistry , crystallography , organic chemistry , physics , catalysis , thermodynamics
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.