oxido-phenyl-phenyliminoazanium

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 85 Parts of an aqueous solution of technical sodium hydrosulfide containing 35 percent NaHS and 9 percent Na2S 2 O3 were added to a mixture comprising 65.4 parts of 2,2'-dichlor-5,5'-dichloroazoxybenzene in 196 parts of methanol at room temperature within 90 minutes. The reaction mixture was then refluxed at 70° C to75° C for a period of 5 hours. The pH had been kept between 9 and 9.4. After this period the starting azoxybenzene was shown to be all consumed and the reaction mixture was cooled down to 0° C to 5° C, and the resulting precipitate filtered off and washed with water until alkali-free. After drying below 70° C 48 parts of 2,2'-dichloro,-5,5'-dichlorohydrazobenzene of a melting point of 116° C were obtained, this representing yield of 76 percent of the theory. at room temperature within 90 minutes all consumed the reaction mixture was cooled down to 0° C to 5° C the resulting precipitate filtered off washed with water until alkali-free After drying below 70° C 48 parts of 2,2'-dichloro

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

Procedure: The reduction reaction was carried out in the same manner as set forth in Example 6 except for using a mixture of 1.0 mmol of o-methyl nitrobenzene and 1.0 mmol of o-ethyl nitrobenzene instead of using nitrobenzene alone, and using 19.5 mg (the amount required for swelling of the reactant in 100%) of Polymer supported reagent-2, and thereby an azoxybenzene derivative of a symmetrical structure and an azoxybenzene derivative of an asymmetrical structure were obtained as a main product, respectively. The reduction reaction

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution containing 10 g of nitrobenzene, 1.27 g of tetramethylammonium hydroxide dihydrate and 1 g of benzonitrile was stirred at 60° C. with nitrogen bubbled into the solution via a syringe needle for 1 hour. Analysis of a sample of the reaction product by HPLC revealed N-(4-nitrophenyl)-benzamide was produced in 45% yield and azoxybenzene was generated in 22% yield based on tetramethylammonium hydroxide. bubbled into the solution via a syringe needle for 1 hour

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

Procedure: The reduction reaction was carried out in the same manner as set forth in Example 6 except for using a mixture of 1.0 mmol of nitrobenzene and 1.0 mmol of o-methyl nitrobenzene instead of using nitrobenzene alone, and using 17 mg (the amount required for swelling of the reactant, i.e., the mixture, in 100%) of Polymer supported reagent-2, and thereby an azoxybenzene derivative of a symmetrical structure and an azoxybenzene derivative of an asymmetrical structure were obtained as a main product, respectively. The reduction reaction

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

Procedure: 0.204 mL (2.0 mmol) of nitrobenzene and either of 17.2 mg (the amount required for swelling of the reactant, nitrobenzene, in 100%) of Polymer supported reagent-1 synthesized in Example 3 or 14 mg (the amount required for swelling of the reactant, nitrobenzene, in 100%) of Polymer supported reagent-2 synthesized in Example 4 were put into a 50 mL, two-neck flask equipped with a water cooler, and the resulting mixture was stirred at a nitrogen atmosphere for 20 minutes to swell the the polymer supported reagent with the reactant. To this were added 0.262 g (4.0 mmol) of Zn powders, 0.214 g (4.0 mmol) of NH4Cl, and 15 mL of distilled water, and then the reduction reaction was conducted at 80° C. for 200 minutes. After the completion of the reaction, 30 mL of an organic solvent, EA was added thereto and stirred at room temperature for 30 minutes. The resulting mixture was then filtered to separate firstly the solid mixture and the liquid mixture solution. The liquid mixture solution as obtained was put into a separating funnel to separate a water layer and an EA layer. To the separated water layer was added 20 mL of EA and stirred to extract the product remained in the water layer. This procedure was repeated 3 times. To the EA solution as combined was added 1.0 g of anhydrous magnesium sulfate and the resulting mixture was stirred for 30 minutes and then filtered. From the filtered EA solution, an excessive amount of EA was evaporated by using an evaporator to obtain azoxybenzene as a main product. supported reagent-1 synthesized in Example 3 or 14 mg (the amount supported reagent-2 synthesized in Example 4 the reduction reaction was conducted at 80° C. for 200 minutes was added stirred at room temperature for 30 minutes The resulting mixture was then filtered to separate firstly the solid mixture The liquid mixture solution as obtained was put into a separating funnel to separate a water layer To the separated water layer was added 20 mL of EA stirred to extract the product To the EA solution as combined was added 1.0 g of anhydrous magnesium sulfate the resulting mixture was stirred for 30 minutes filtered From the filtered EA solution, an excessive amount of EA was evaporated an evaporator

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

Procedure: The reduction reaction was carried out in the same manner as set forth in Example 6 except for using a mixture of 1.0 mmol of nitrobenzene and 1.0 mmol of o-ethyl nitrobenzene instead of using nitrobenzene alone, and using 16.5 mg (the amount required for swelling of the reactant, i.e., the mixture, in 100%) of Polymer supported reagent-2, and thereby an azoxybenzene derivative of a symmetrical structure and an azoxybenzene derivative of an asymmetrical structure were obtained as a main product, respectively. Besides, a small amount of an azobenzene derivative of a symmetrical structure was also synthesized. The reduction reaction

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution containing 10 g of nitrobenzene, 1.27 g of tetramethylammonium hydroxide dihydrate and 1 g of benzonitrile was stirred at 60° C. with nitrogen bubbled into the solution via a syringe needle for 1 hour. Analysis of a sample of the reaction product by HPLC revealed N-(4-nitrophenyl)-benzamide was produced in 45% yield and azoxybenzene was generated in 22% yield based on tetramethylammonium hydroxide. bubbled into the solution via a syringe needle for 1 hour

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 85 Parts of an aqueous solution of technical sodium hydrosulfide containing 35 percent NaHS and 9 percent Na2S 2 O3 were added to a mixture comprising 65.4 parts of 2,2'-dichlor-5,5'-dichloroazoxybenzene in 196 parts of methanol at room temperature within 90 minutes. The reaction mixture was then refluxed at 70° C to75° C for a period of 5 hours. The pH had been kept between 9 and 9.4. After this period the starting azoxybenzene was shown to be all consumed and the reaction mixture was cooled down to 0° C to 5° C, and the resulting precipitate filtered off and washed with water until alkali-free. After drying below 70° C 48 parts of 2,2'-dichloro,-5,5'-dichlorohydrazobenzene of a melting point of 116° C were obtained, this representing yield of 76 percent of the theory. at room temperature within 90 minutes all consumed the reaction mixture was cooled down to 0° C to 5° C the resulting precipitate filtered off washed with water until alkali-free After drying below 70° C 48 parts of 2,2'-dichloro