Short-RInChIKey=SA-FUHFF-UHFFFADPSC-YBGSMMQIEM-UHFFFADPSC-NUHFF-NOCXD-NUHFF-ZZZ

N-Benzylideneaniline (906 mg, 5.00 mmol, 1.00 equiv) and sodium;cyanide (49.0 mg, 1.00 mmol, 0.200 equiv) was evacuated in a schlenk tube. N,N-dimethylformamide (30.0 mL) was added and stirred for 24 h at room temperature under argon. After that, 100 mL of DCM was added and the mixture was extracted with water (3 times 100 mL). 1,4-Benzoquinone (540 mg, 5.00 mmol, 1.00 equiv) was added and stirred for 2 h at 25 °C and open air. After that, the mixture was filtered, extracted with water (3 times 50 mL) and the aqueous layers were extracted with DCM (3 times 50 mL). The organic layers were dried with MgSO4, filtered and evaporated. After recrystallization in MeOH (10 mL), N,N',1,2-tetraphenylethane-1,2-bisimine (432 mg, 1.20 mmol, 24% yield) was obtained as yellow crystals.