Journal of the Chemical Society. Perkin transactions II p. 583 - 588 (1984)
Update date:2022-08-11
Topics:
Bailey, Judith M.
Booth, Harold
Al-Shirayda, Hatif A. R. Y.
The position of conformational equilibria due to ring inversion in N-alkyl-cis-decahydroisoquinolines (alkyl = Me, Et, Pri, CH2CF3, or CH2CCl3) has been assessed directly from 13C and/or 19F n.m.r. spectra recorded at temperatures between 173 and 253 K.The measured equilibrium constants are related to the inductive effect of the N-substituent which produces an increase (Me, Et, Pri) or decrease (CH2CF3, CH2CCl3) in the magnitude of the gauche propylamine-type repulsive interaction. 13C Chemical shifts are tabulated for the carbon atoms of the two twin-chair conformations undergoing exchange.
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