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

Avenati Marco | Zendy; Pilet Olivier | Zendy; Carrupt PierreAlain | Zendy; Vogel Pierre | Zendy

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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

Author(s) -

Avenati Marco,

Pilet Olivier,

Carrupt PierreAlain,

Vogel Pierre

Publication year - 1982

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19820650117

Subject(s) - chemistry , octane , reactivity (psychology) , tetracyanoethylene , bicyclic molecule , toluene , medicinal chemistry , cycloaddition , stereochemistry , organic chemistry , catalysis , alternative medicine , pathology , medicine

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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