Ravi S. Orugunty, I. Ghiviriga, K. Abboud
Jan 23, 2004
Citations
0
Influential Citations
19
Citations
Journal
The Journal of organic chemistry
Abstract
The reaction of tetrabromocyclopropene and furan leads directly to 8-oxabicyclo[3.2.1]octadiene derivatives. It has been proposed that this involves an initial Diels-Alder reaction followed by rearrangement of the primary adduct. We have, for the first time, isolated a primary adduct and established through X-ray crystallographic analysis that the adduct is the product of an exo-selective addition. Kinetic studies suggest the intermediacy of charged intermediates during the rearrangement.