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The conformation of 4-phenylcyclohexanone in solution by1H- and13C-Lanthanide induced shift (L.I.S.) analysis : Evidence in favour of phenyl over t-butyl as a conformational lock

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
22
Issue
29
Identifiers
DOI: 10.1016/s0040-4039(01)90558-1

Abstract

Abstract The degree of pucker of the cyclohexanone ring in 4-phenylcyclohexanone has been refined by L.I.S. analysis. The results indicate puckering intermediate between that in cyclohexanone and 4-t-butylcyclohexanone, suggesting that phenyl may be preferable to t-butyl as a locking group in conformational analysis. The Yb (fod)3 shift reagent, although binding primarily at the carbonyl oxygen atom, also complexes weakly with the phenyl group.

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