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Conformation of non-aromatic ring compounds: Part 56. The conformational properties of cis-2-halogeno-4-t-butylcyclohexanones

✍ Scribed by H. R. Buys; M. T. Giesen; E. Havinga

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
302 KB
Volume
89
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

The dipole moments and vicinal coupling constants of cis‐2‐bromo‐, cis‐2‐chloro‐ and cis‐2‐fluoro‐4‐t‐butylcyclohexanone have been determined in several solvents, in order to investigate the conformational homogeneity of these compounds. The dipole moments show a small solvent‐dependence, which is not reflected in the coupling constants. The results can be explained satisfactorily on the assumption that in the solutions only the chair form (with an equatorially oriented halogen atom) occurs.

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In a previous paper (2) the conformation81 features of six 2-alkoxytetrahydropyrans (Fig. 1, R = Me, Et, n-Pr, i-Pr, n-Bu, t-Bu) were discussed on the baais of dipole moment and NMR results. The main conclusions concerning the conformational equilibrium and the