Abstract
The dimerization of benzocyclobutadiene (1), generated by the fluoride ion-induced elimination of trimethylsilyl mesylate from 2-(trimethylsilyl)benzocyclobutenyl-1 mesylate (5), was carefully studied by flow NMR spectroscopy. Only formation of the final dimer, 6a,10b-dihydrobenzo[a]-biphenylene (2), was observed; no evidence for the formation of transient intermediates was obtained. Benzocyclobutadiene with a deuterium atom on position 1, 1-d{sub 1}, was prepared and allowed to dimerize. It is shown by several NMR spectroscopic techniques that 1-d{sub 1} dimerizes to produce six dideuterated isotopomers. It is proposed that the deuterium distribution is explained by a dimerization mechanism involving the formation of [4 + 2] dimer 3 followed by opening of 3 to form dibenzo[a,d]cyclooctatetraene (6) which closes to final dimer 2. 13 refs., 3 figs.
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