Bridged synthons from tetrabromocyclopropene: studies on the rearrangement of the primary Diels-Alder adduct with 2,5-dimethylfuran

Ravi S Orugunty; Ion Ghiviriga; Khalil A Abboud; Merle A Battiste; Dennis L Wright

doi:10.1021/jo0352631

Bridged synthons from tetrabromocyclopropene: studies on the rearrangement of the primary Diels-Alder adduct with 2,5-dimethylfuran

J Org Chem. 2004 Jan 23;69(2):570-2. doi: 10.1021/jo0352631.

Authors

Ravi S Orugunty¹, Ion Ghiviriga, Khalil A Abboud, Merle A Battiste, Dennis L Wright

Affiliation

¹ Department of Chemistry, University of Florida, Gainesville, Florida 32606, USA.

PMID: 14725477
DOI: 10.1021/jo0352631

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.