The only valence isomer of benzene not previously prepared has now been synthesized by reaction in vacuo of the β-halosilane 1 with tetra-n-butylammonium fluoride. The elusive bicycloprop-2-enyl 2 was characterized by NMR spectroscopy. 2 can also be trapped as a Diels-Alder adduct. In the presence of Ag⊕ it rearranges to Dewar benzene.
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Billups et al. (1989) studied this question.
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