1,4-diazidobutane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3.95 g (25 mmoles) of 2-bromopyridine in 20 ml of dry pentane was added dropwise to 10 ml. of 2.5M butylithium in hexane at -78° C. To the resulting yellow slurry was added dropwise with stirring 1.75 g (12.5 mmoles) of 1,4-diazidobutane in 10 ml. of pentane. Stirring was continued for 2 hr. at -78° and then the reaction mixture was allowed to warm to room temperature. The reaction mixture was treated with 60 ml. of ammonium buffer which caused a precipitate to appear after the reaction was cooled to -78° C. The solid was filtered off. It was poorly soluble in common solvents such as halomethanes, acetone, methanol and water. It was sparingly soluble in dimethylsulfoxide. The yield was 2.3 g., m.p. 133-136. Spectroscopic data were consistent with the structure. at -78° C To the resulting yellow slurry was added dropwise at -78° The reaction mixture was treated with 60 ml was cooled to -78° C The solid was filtered off

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3.95 g (25 mmoles) of 2-bromopyridine in 20 ml of dry pentane was added dropwise to 10 ml. of 2.5M butylithium in hexane at -78° C. To the resulting yellow slurry was added dropwise with stirring 1.75 g (12.5 mmoles) of 1,4-diazidobutane in 10 ml. of pentane. Stirring was continued for 2 hr. at -78° and then the reaction mixture was allowed to warm to room temperature. The reaction mixture was treated with 60 ml. of ammonium buffer which caused a precipitate to appear after the reaction was cooled to -78° C. The solid was filtered off. It was poorly soluble in common solvents such as halomethanes, acetone, methanol and water. It was sparingly soluble in dimethylsulfoxide. The yield was 2.3 g., m.p. 133-136. Spectroscopic data were consistent with the structure. at -78° C To the resulting yellow slurry was added dropwise at -78° The reaction mixture was treated with 60 ml was cooled to -78° C The solid was filtered off

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3.95 g (25 mmoles) of 2-bromopyridine in 20 ml of dry pentane was added dropwise to 10 ml. of 2.5M butylithium in hexane at -78° C. To the resulting yellow slurry was added dropwise with stirring 1.75 g (12.5 mmoles) of 1,4-diazidobutane in 10 ml. of pentane. Stirring was continued for 2 hr. at -78° and then the reaction mixture was allowed to warm to room temperature. The reaction mixture was treated with 60 ml. of ammonium buffer which caused a precipitate to appear after the reaction was cooled to -78° C. The solid was filtered off. It was poorly soluble in common solvents such as halomethanes, acetone, methanol and water. It was sparingly soluble in dimethylsulfoxide. The yield was 2.3 g., m.p. 133-136. Spectroscopic data were consistent with the structure. at -78° C To the resulting yellow slurry was added dropwise at -78° The reaction mixture was treated with 60 ml was cooled to -78° C The solid was filtered off

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1.40 g (10 mmoles) of 1,4-diazidobutane, in 10 ml. of THF and chilled to -45° C., was treated dropwise with 15 ml of 2.0M benzylmagnesium chloride in THF (30 mmoles). The reaction mixture was magnetically stirred overnight at room temperature. The solvent was removed under vacuum and the residue was dissolved in 200 ml. of diethylether and washed with 30 ml. of ammonium buffer (50 g. ammonium chloride, 178 ml. of 10% ammonium hydroxide and 272 ml. of water), followed by 2×30 ml of water. The solution was dried over sodium sulfate and concentrated on a rotary evaporator and dried under high vacuum at room temperature. The crude product was recrystallized from diethylether in the -20° freezer to produce 2.6 g. of white crystals m.p. 71°-74° C. The nmr and mass spectra were fully consistent with the structure. The solvent was removed under vacuum the residue was dissolved in 200 ml of diethylether and washed with 30 ml The solution was dried over sodium sulfate concentrated on a rotary evaporator dried under high vacuum at room temperature The crude product was recrystallized from diethylether in the -20° freezer to produce 2.6 g