New acenaphthene-1,2-diimine and its reduction to the tetraanion. Molecular structures of 1,2-bis[(trimethylsilyl)imino]acenaphthene and its lithium derivatives
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- Fedushkin, I.L., Khvoinova, N.M., Piskunov, A.V. et al. Russ Chem Bull (2006) 55: 722. doi:10.1007/s11172-006-0320-1
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1,2-Bis[(trimethylsilyl)imino]acenaphthene (1) was synthesized by the reaction of acenaphthenequinone with (Me3Si)2NLi in toluene followed by treatment of the reaction product with trimethylchlorosilane. The dianionic derivative [(tms-BIAN)Li2]2 (3) was obtained as the final product by reduction of compound 1 with lithium in toluene, whereas reduction in diethyl ether afforded the tetraanion [(tms-BIAN)Li4(Et2O)3]2 (5). The formation of the paramagnetic mono-and trianions in solution was confirmed by ESR spectroscopy. Compounds 3 and 5 were isolated in the crystalline state and characterized by elemental analysis, IR spectroscopy, and NMR spectroscopy. The crystal structures of 1, 3, and 5 were established by X-ray diffraction.