Attempted preparation of 1  by reduction of the unsaturated precursor gave over-reduction to a tetraanion with the antiaromatic dianion present as well in the quench of the reaction mixture. The NMR spectrum of the reaction mixture showed only tetraanion, which may be due to the small HOMO-LUMO gap of the antiaromatic species. We report the synthesis of 1  through deprotonation of the appropriate saturated precursor and confirm its NMR spectral invisibility, as well as the synthesis of precursors to dianions 2  and 3  along with preliminary spectra of 2  and 3 .

Effect of benzannulation on the antiaromaticity of cycloheptatrienyl anions

245th National Meeting (2013)

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