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The Configuration of Tricyclo [7.1.1.02,7]undecanes and the Stereochemistry of the Reduction of Tricyclone

✍ Scribed by Alan F. Thomas; Walter Thommen; Josef Becker

Book ID: 102859073
Publisher: John Wiley and Sons
Year: 1981
Tongue: German
Weight: 616 KB
Volume: 64
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19810640116

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✦ Synopsis

Abstract

A full discussion of the configuration of tricyclo [7.1.1.0^2,7^]undecanes related to cis‐10, 10‐dimethyltricyclo [7.1.1.0^2,7^]undec‐2‐en‐4‐one (2), the Robinson annelation product from norpinone 1 and 3‐buten‐2‐one is given, based on 360‐MHz‐NMR. spectra. Nuclear Overhauser effects confirm the cis configuration of 2, and show that the saturated ketone 10, obtained by catalytic hydrogenation, is also all‐cis with the cyclohexanone ring in the boat conformation. The parent hydrocarbon, cis‐10, 10‐dimethyltricyclo[7.1.1.0^2,7^]undecane is compared with one of the corresponding trans isomers prepared from pinocarvone (14). The stereochemistry of metal hydride reduction and Grignard reaction of 2 is examined.

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