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research article
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).
Type
research article
Authors
Publication date
1992
Published in
Volume
75
Issue
4
Start page
1085
End page
1094
Note
Univ lausanne,chim sect,rue barre 2,ch-1005 lausanne,switzerland.
Peer reviewed
REVIEWED
EPFL units
Available on Infoscience
November 9, 2005
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