The Diels-Alder Chemoselectivity of 3,4,6,7-Tetramethylidenebicyclo[3.2.1]Octane-2-Exo,8-Syn-Diyl Derivatives

Strong dienophiles prefer to add onto the diene moiety attached at C(2),C(3) of 2,3,6,7-tetramethylidenebicyclo[3,2,1]octane ((+/-)-1; see Scheme 1), whereas in the case of 3,4,6,7-tetramethylidenebicyclo[3.2.1]octane-2-exo,8-syn-diyl derivatives. the diene moiety at C(6),C(7) reacts faster than that at C(3),C(4), as long the bulk of the 8-syn-substituent is large enough (see Schemes 2 and 3).


Published in:
Helvetica Chimica Acta, 75, 4, 1085-1094
Year:
1992
ISSN:
0018-019X
Keywords:
Note:
Univ lausanne,chim sect,rue barre 2,ch-1005 lausanne,switzerland.
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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