Diphenyl-s-tetrazine

Uses3,6-Diphenyl-1,2,4,5-tetrazine may be used in the preparation of dihydropyridazine derivatives, via reaction with cis,cis-cycloocta-1,5-diene.

General Description3,6-Diphenyl-1,2,4,5-tetrazine is an an electron-deficient heteroaromatic azadiene. It participates in inverse electron demand cycloaddition reactions with various dienophiles. It is reported to participate in facile inverse electron demand Diels-Alder reactions with “tunable” reaction rates. The electron transport characteristics of 3,6-diphenyl-1,2,4,5-tetrazine (DPT) single molecular conductor have been studied by density functional theory (DFT) method. Basicity of 3,6-diphenyl-1,2,4,5-tetrazine in aqueous solutions of sulfuric acid (pKBH+) is -4.8. It undergoes thermal Diels-Alder reaction with C60 to afford monoadducts, possessing a diaryldihydropyridazine function nested atop the fullerene.

PreparationA mixture of benzonitrile (84 mmol) and 95% hydrazine (100 mL) is heated at 100 °C for 72 h. The resulting orange-yellow solid is broken up, washed with H2O, air dried, ground to a fine powder, and added to 100 mL of 10% acetic acid. Small portions of sodium nitrite are added to this solution while warming at 100 °C for 1 h. 3,6-DIPHENYL-1,2,4,5-TETRAZINE thus produced is collected, washed with H2O, and recrystallized from EtOH.