Y. Taskesenligil et al., An investigation of the formation mechanism of allene or alkyne in the 6,7-benzobicyclo[3,2.1]octane system by deuterium labeling experiments, TURK J CHEM, 23(2), 1999, pp. 115-122
In order to reveal the real intermediate in the base-promoted reaction of 1
, 3-bromo-4,4-dideuterio-6,7-benaobicyclo[3.2.1]octa-2,6-diene 10 was synth
esized and its HBr elimination reaction studied. Reaction of 10 with potass
ium tert-butoxide yielded butoxyl ether 18 in which proton-deuterium exchan
ge has occured.