Lithium 4,4′-Di-tert-butylbiphenylide

[61217-61-6] C20H26Li (MW 273.40) InChI = 1S/C20H26.Li/c1-19(2,3)17-11-7-15(8-12-17)16-9-13-18(14-10-16)20(4,5)6;/h7-14H,1-6H3;/q-1;+1 InChIKey = DAPBZLVFPGDJEE-UHFFFAOYSA-N (reductive lithiations of thiophenyl ethers,11 carbonyl groups,23 phosphinates;25 generation of alkyllithiums,2α-lithio ethers,3 allyllithiums,17, 18β-,γ-,δ-lithio alkoxides;19 propellane bond cleavage22) Alternate Name: LDBB. Solubility: sol THF Preparative Methods: anhydrous THF and 4,4′-di-t-butylbiphenyl (DBB) are cooled to 0 °C under a blanket of argon and stirred with a glass-coated stirring bar; Lithium foil (or ribbon) is added in portions and the mixture is stirred for 5 h at 0 °C; the appearance of the deep blue-green radical anion appears within 5 min. Handling, Storage, and Precautions: LDBB will slowly decompose at room temperature.