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Interaction between Exocyclic s-cis-Butadiene and Homoconjugated Functions. Preparation and Diels-Alder Reactivity of Remotely Substituted 2,3-Dimethylidenebicyclo[2.2.2]octanes

✍ Scribed by Marco Avenati; Olivier Pilet; Pierre-Alain Carrupt; Pierre Vogel

Publisher: John Wiley and Sons
Year: 1982
Tongue: German
Weight: 666 KB
Volume: 65
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19820650117

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✦ Synopsis

Abstract

The preparations of 5,6‐dimethylidene‐2__exo__‐bicyclo[2.2.2]octanol (8), its endo isomer 9, 5,6‐dimethylidene‐2‐bicyclo[2.2.2]octanone (10) and 2 exo, 3 exo‐epoxy‐5,6dimethylidenebicyclo[2.2.2]octane (11) are described. The kinetics of their cycloaddition to tetracyanoethylene has been measured in toluene at 25° together with those of 2,3‐dimethylidenebicyclo[2.2.2]octane (7) and 5,6‐dimethylidenebicyclo[2.2.2]oct‐2‐ene (12). The effects of remote substitution on the Diels‐Alder reactivity of 2,3‐dimethyl idenebicyclo[2.2.2]octanes are compared with those observed in the 2,3‐dimethylidenenorbornane series (1–6).

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✍ Jean-Pierre Hagenbuch; Jean-Luc Birbaum; Jean-Luc Métral; Pierre Vogel 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 German ⚖ 640 KB

## Abstract The rates of photo‐oxidation of exocyclic __S‐cis__‐butadienes grafted onto bicyclo‐[2.2.1]heptanes and 7‐oxabicyclo[2.2.1]heptanes (**1–6**) are dependent upon remote modifications of the bicyclic skeletons. They correlate with the rates of __Diels‐Alder__ additions of these dienes to