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A New Family of Tropylium Ions: Tropone–Triarylborane Complexes

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Air- and thermally stable tropone–triarylborane 1:1 complexes were synthesized in excellent yields by treating tropones, including benzo-fused derivatives, with an equimolar amount of B(C6F5)3. NMR and X-ray analyses and DFT calculations revealed that the tropone–triarylborane complexes have betaine structures consisting of tropylium and borate moieties and that their aromaticity depends on the number of fused benzene rings.


Abstract

Air- and thermally stable tropone–triarylborane 1 : 1 complexes were synthesized in excellent yields by treating tropones, including benzo-fused derivatives, with an equimolar amount of B(C6F5)3. NMR and X-ray analyses and DFT calculations including nuclear independent chemical shift (NICS) and anisotropy of the induced current density (ACID) studies revealed that the tropone–triarylborane complexes have betaine structures consisting of tropylium and borate moieties and that their aromaticity depends on the number of fused benzene rings.

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