TETRAHYDROPENTALENE-2,5-DIONE

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Compound [I-c] was synthesized in the same manner as in Synthesis Example (5) except that 1,4-cyclohexanedione was replaced by 27.6 g (0.2 mole) of bicyclo[3.3.0]octane-3,7-dione (m.p. 85° C.).

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

Procedure: To bicyclo[3.3.0]octane-3,7-dione (0.25 g, 1.81 mmol) in dry MeOH (3 mL) at 0° C. was added hydroxylamine hydrochloride (0.28 g, 4.30 mmol) and NaOAc (0.65 g, 7.92 mmol). After 1 h, the solvent was removed under vacuum. Triturate the resulting residue with a minimum of ice-cold water to give a white precipitate. Collect and dry the precipitate under vacuum to give 0.16 g of the crude oxine. the solvent was removed under vacuum Triturate the resulting residue with a minimum of ice-cold water to give a white precipitate Collect dry the precipitate under vacuum

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

Procedure: To bicyclo[3.3.0]octane-3,7-dione (0.25 g, 1.81 mmol) in dry MeOH (3 mL) at 0° C. was added hydroxylamine hydrochloride (0.28 g, 4.30 mmol) and NaOAc (0.65 g, 7.92 mmol). After 1 h, the solvent was removed under vacuum. Triturate the resulting residue with a minimum of ice-cold water to give a white precipitate. Collect and dry the precipitate under vacuum to give 0.16 g of the crude oxine. the solvent was removed under vacuum Triturate the resulting residue with a minimum of ice-cold water to give a white precipitate Collect dry the precipitate under vacuum

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: In a 300-cm3 four-necked flask in which the atmosphere was replaced with nitrogen, 4.9 g of bicyclo[3,3,0]octane-3,7-dione and 12 g of cyclopentadiene were dissolved in 100 cm3 of methanol. 12 cm3 of pyrrolidine was added dropwise to the solution at 0° C. over 30 minutes, and the produced solid was collected by filtration, washed with methanol, and then dried to obtain 5.3 g of yellow 3,7-biscyclopentadienylidenebicyclo[3,3,0]octane. [3,7-dicyclopentadienyl-3,7-difluorenylbicyclo[3,3,0]octane] the produced solid was collected by filtration washed with methanol dried

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

Procedure: In a 300-cm3 four-necked flask in which the atmosphere was replaced with nitrogen, 4.9 g of bicyclo[3,3,0]octane-3,7-dione and 12 g of cyclopentadiene were dissolved in 100 cm3 of methanol. 12 cm3 of pyrrolidine was added dropwise to the solution at 0° C. over 30 minutes, and the produced solid was collected by filtration, washed with methanol, and then dried to obtain 5.3 g of yellow 3,7-biscyclopentadienylidenebicyclo[3,3,0]octane. the produced solid was collected by filtration washed with methanol dried

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

Procedure: 1.1 g of sodium borohydride (0.029 mol) is added with stirring to a solution of 11.6 g of bicyclo[3.3.0]octane-3,7-dione (8.4×10-2 mol) in 100 ml of methylene chloride and 100 ml of ethanol. After 45 minutes at this temperature, the excess reagent is decomposed by slowly adding 20 ml of acetone. The mixture is then neutralized with 1.4 ml of acetic acid, and evaporated under vacuum to afford a residue which is taken up in water and methylene chloride. The organic phase is evaporated to dryness and filtered on silica gel (70:30 hexane:ethyl ether as eluent) to afford 9.1 g of 7ξ-hydroxy-bicyclo[3.3.0]octan-3-one. evaporated under vacuum to afford a residue which The organic phase is evaporated to dryness filtered on silica gel (70:30 hexane:ethyl ether as eluent)

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

Procedure: Compound [I-c] was synthesized in the same manner as in Synthesis Example (5) except that 1,4-cyclohexanedione was replaced by 27.6 g (0.2 mole) of bicyclo[3.3.0]octane-3,7-dione (m.p. 85° C.).

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

Procedure: To bicyclo[3.3.0]octane-3,7-dione (0.25 g, 1.81 mmol) in dry MeOH (3 mL) at 0° C. was added hydroxylamine hydrochloride (0.28 g, 4.30 mmol) and NaOAc (0.65 g, 7.92 mmol). After 1 h, the solvent was removed under vacuum. Triturate the resulting residue with a minimum of ice-cold water to give a white precipitate. Collect and dry the precipitate under vacuum to give 0.16 g of the crude oxine. the solvent was removed under vacuum Triturate the resulting residue with a minimum of ice-cold water to give a white precipitate Collect dry the precipitate under vacuum