An investigation of the formation mechanism of allene or alkyne in the 6, 7-benzobicyclo (3.2.1) octane system by deuterium labeling experiments

Abstract

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.