Keywords
‘double’ donor–acceptor cyclopropanes
alkenes
Annulation
cycloaddition
dienes
gallium trichloride
polycyclic carbocycles.
Abstract
The reactions of ‘double’ donor-acceptor cyclopropanes containing a p- or m-phenylene moiety with alkenes or dienes in the presence of GaCl3 comprise formation of gallium 1,2-zwitterionic intermediates, the structure of final products being substrate dependent. In contrast to the para-or meta-isomers, reaction of 2,2'-(1,2-phenylene)bis(cyclopropane-1,1-dicarboxylate) does not involve alkene and affords isomeric tricyclo[6.2.2.02,7]dodeca-2,4,6-triene-9,9,11,11-tetra-carboxylate, a product of intramolecular rearrangement.
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