[structure: see text] Benzene and 1,2-dichloroethane solutions of the Li(+) salt of the weakly coordinating anion CB(11)Me(12)(-) catalyze the rearrangement of cubane to cuneane, quadricyclane to norbornadiene, basketene to Nenitzescu's hydrocarbon, and diademane to triquinacene. The Claisen rearrangement of phenyl allyl ether is also strongly accelerated.

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Abstract:The reaction of MgCOT(thf), with tBuBF, or PhBCl, affords the first 9-borabarbaralanes 2 (C,H,BR, a: R = tBu; b: R =Ph). With the aminoboron dihalides BCI,NiPr, and BCI,N(SiMe,)tBu 9-borabicyclo[4.2.1]-nona-2,4,7-trienes 3 (a: R = NiPr,, b: R = N(SiMe,)tBu) and the trans-9-borabicyclo[4.3.0]nona-2,4,7-triene 4 are obtained. The bicyclic compounds 3 a and 3 b are converted into 9-borabarbaralanes

LiCB 11 Me 12 : A Catalyst for Pericyclic Rearrangements. -Benzene or 1,2-dichloroethane solutions of the lithium salt of the weakly coordinating anion CB 11 Me 12 − catalyze the rearrangement of cubane to cuneane, quadricyclane to norbornadiene, basketene to Nenitzescu's hydrocarbon, and diademane to triquinacene. The Claisen rearrangement of phenyl allyl ether is also strongly accelerated. The reactions are monitored by NMR. The half-lives for the isomerizations are given. -(MOSS, STEFAN; KING, BENJAMIN T.; DE MEIJERE, ARMIN; KOZHUSHKOV, SERGEI I.; EATON, PHILIP E.; MICHL, JOSEF; Org. Lett. 3 (2001) 15, 2375-2377; Dep. Chem. Biochem., Univ. Colo., Boulder, CO 80309, USA; EN)