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The conformation of (1R,2S,4R,5S)-2,4-dimethoxybicyclo[3.3.1]nonan-9-one and some related compounds

✍ Scribed by P. Camps; C. Jaime

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

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✦ Synopsis

Abstract

A mixture of stereoisomers of 2,4‐dimethoxybicyclo[3.3.1]nonan‐9‐one was prepared, separated by column chromatography and characterized by 60 MHz ^1^H NMR spectroscopy using Eu(fod)~3~. A double chair conformation with axial methoxyl groups is established for (1__R__,2__S__,4__R__,5__S__)‐2,4‐dimethoxybicyclo[3.3.1]‐nonan‐9‐one on the basis of the J(12), J(2,H‐3 exo) and J(2,3 endo) values and the chemical shifts for H‐2(4). The conformation of some related compounds is subsequently inferred.

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