Mikhailov, B. M. published the artcileOrganoboron compounds. Synthesis of complex compounds of unsymmetric borontriaryls, COA of Formula: C23H20BN, the publication is Doklady Akademii Nauk SSSR (1956), 94-7, database is CAplus.
All operations with Li derivatives described below were performed under N. To 0.07 mol 1-C10H7Li in Et2O was added at -10° in 1 h. 16.6 g. Ph2BOCH2CHMe2; after 2 h. at room temperature there was obtained a precipitate of 30% [Ph2(1-C10H7)BOCH2CHMe2]Li.2Et2O (I), a crystalline solid. The filtrate from this was treated with NH3 yielding 30% 1-C10H7BPh2.NH3, a solid (from C6H6-pentane). Similarly, 0.028 mol PhLi and 9.4 g. iso-BuOB(C10H7-1)2 gave 80% [(1-C10H7)2BPhOCH2CHMe2]Li (II). I (0.9 g.) in Et2O-C6H6 was treated with 0.5 mL. pyridine; after evaporation the residue was treated with H2O yielding an insoluble precipitate of 88% [Ph2B(1-C10H7)].C5H5N, m. 170-5°. Similarly, II gave 80% (1-C10H7)2BPh.C5H5N, m. 213-15°. Similarly was prepared 46% (1-C10H7)2(o-MeC6H4)B.C5H5N, m. 203-5°. Passage of NH3 into II in Et2O gave after evaporation of solvent and dilution with H2O 75% insoluble (1-C10H7)2BPh.NH3, m. 170-3° (shrinks at 135-44°). From o-MeC6H4Li and iso-BuOBPh2 was prepared the complex Li salt (IIa) which treated with NH3 in Et2O gave 54.5% (o-MeC6H4)BPh2.NH3, m. 175-8° (shrinks at 147-50°), while the filtrate on addition of KBr gave o-MeC6H4BPh2K, colorless crystals. Similarly, PhLi and iso-BuOBPh2 gave 65% Ph3B.NH3, m. 202-4°, while the filtrate with KBr gave a little Ph4BK. Passage of dry HCl into I in C6H6, filtration and evaporation gave a residue which taken up in pentane and treated with NH3 gave 97% Ph2BOCH2CHMe2.NH3 (III), m. 101-3°, while the filtrate gave C10H8; III, m. 103-5°, forms from NH3 and the ester directly. Similarly IIa treated with HCl, then with NH3 as above gave 70% III. Treatment of III with 1 mol PhLi in Et2O gave 50% Ph3B.NH3. Addition of 0.0043 mol iso-BuOBPh2 to 0.005 mol PhLi without cooling in Et2O followed by 1 mol pyridine rapidly gave 96% Ph3B.C5H5N, decompose 215°. Similarly were prepared o-MeC6H4BPh2.C5H5N, m. 172-4°, and 85% (1-C10H7)2(o-MeC6H4)B.C5H5N, m. 203-5°.
Doklady Akademii Nauk SSSR published new progress about 971-66-4. 971-66-4 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene, name is Triphenyl(pyridin-1-ium-1-yl)borate, and the molecular formula is C23H20BN, COA of Formula: C23H20BN.
Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem