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Pyramidalized olefins: The stereospecific conjugate reduction of a bicyclo[2.2.2]octadiene

✍ Scribed by Richard Vaughan Williams; Vijay R. Gadgil; Gary G. Garner; John D. Williams; Ashwani Vij

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
107 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Structure determination on 2-benzenesulphonyl-3-trimethylsilylbicyclo[2.2.2]octa-2,5-diene (3) demonstrates that the double bonds are pyramidalized in the exo direction. Nucleophilic attack (conjugate reduction) on 3 parallels this pyramidalization and occurs exclusively from the endo face.

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