In order to reveal the real intermediate in the base-promoted reaction of 1, 3-bromo-4,4-dideuterio-6,7-benzobicyclo[3.2.1]octa-2,6-diene 10 was synthesized and its HBr elimination reaction studied. Reaction of 10 with potassium tert-butoxide yielded butoxyl ether 18 in which proton-deuterium exchange has occured.
TAŞKESENLIGIL, YAVUZ; TÜMER, FERHAN; KAZAZ, CAVİT; and BALCI, METİN (1999) "An Investigation of the Formation Mechanism of Allene or Alkyne in the 6,7-Benzobicyclo[3.2.1]octane System by Deuterium Labeling Experiments," Turkish Journal of Chemistry: Vol. 23: No. 2, Article 1. Available at: https://journals.tubitak.gov.tr/chem/vol23/iss2/1