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Laali, K.K.* ; Okazaki, T.* ; Bunge, S.D.* ; Lenoir, D.

Stable ion and electrophilic chemistry of the sterically crowded stilbene 1,1'-Bi(benzocyclobutenylidene) and its derivatives.

J. Org. Chem. 73, 4092-4100 (2008)

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Generation and NMR studies of novel carbocations and carboxonium ions are reported from sterically hindered stilbene 1,1'-bi(benzocyclobutenylidene) 1, its dimethoxy derivative 5, and from their skeletally rearranged derivatives, namely, the spirocyclic ketone 6, diastereomeric alcohols 7 and isomeric diols 8. Quenching experiments on the carbocations under various conditions resulted in the formation/isolation of several novel covalent adducts. Acid-catalyzed isomerization of the diols 8 produced a remarkable dimeric molecule, whose structure was confirmed by X-ray analysis. Reactions of hindered stilbenes 1 and 5 with Br 2/CDCl 3 were examined via NMR experiments. The experimentally observed carbocations were also studied computationally by GIAO-DFT and by NICS.

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