N-cyclooctylidenehydroxylamine

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

Procedure: A solution containing cyclooctanone oxime (9.0 g, 64 mmol) in glacial acetic acid (90 mL) was slowly charged with sodium cyanoborohydride (6.0 g, 95 mmol). The reaction mixture was stirred at ambient temperature for 18 hours then adjusted to pH=9 by the slow addition of cold 2N sodium hydroxide. The resulting precipitate was collected and dried to provide cyclooctyl hydroxylamine as a white solid. The resulting precipitate was collected dried

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

Procedure: A solution containing cyclooctanone oxime (9.0 g, 64 mmol) in glacial acetic acid (90 mL) was slowly charged with sodium cyanoborohydride (6.0 g, 95 mmol). The reaction mixture was stirred at ambient temperature for 18 hours then adjusted to pH=9 by the slow addition of cold 2N sodium hydroxide. The resulting precipitate was collected and dried to provide cyclooctyl hydroxylamine as a white solid. The resulting precipitate was collected dried

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

Procedure: A solution containing cyclooctanone (12.6 g, 0.1 mol) and hydroxylamine hydrochloride (14.0 g, 0.2 mole) in a mixture of pyridine (40 mL, 0.5 mole) and ethanol (50 mL) was stirred at ambient temperature for about 15 hours. The solvent was then removed by rotary evaporation. The residue was dissolved in diethyl ether (300 mL) then washed with hydrochloric acid (2×100 mL). The aqueous layer was extracted with diethyl ether (2×150 mL). The ether extracts were combined, dried over magnesium sulfate then concentrated to provide cyclooctanone oxime as a white solid. The solvent was then removed by rotary evaporation The residue was dissolved in diethyl ether (300 mL) then washed with hydrochloric acid (2×100 mL) The aqueous layer was extracted with diethyl ether (2×150 mL) dried over magnesium sulfate then concentrated

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclooctane (2 ml), t-butyl nitrite (1 mmol), N-hydroxyphthalimide (0.2 mmol), and acetic acid (1 ml) were placed in a flask and were stirred at 80° C. in an atmosphere of argon gas (1 atm=0.101 MPa) for 20 hours. The resulting reaction mixture was analyzed to find that cyclooctanone oxime, nitrocyclooctane, and cyclooctanone were formed in yields of 64%, 4%, and 2%, respectively. The resulting reaction mixture

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclooctane (1 ml), t-butyl nitrite (1 mmol), N-hydroxyphthalimide (0.2 mmol), and acetic acid (1 ml) were placed in a flask and were stirred at 80° C. in an atmosphere of argon gas (1 atm=0.101 MPa) for 20 hours. The resulting reaction mixture was analyzed to find that cyclooctanone oxime, nitrocyclooctane, and cyclooctanone were formed in yields of 55%, 5%, and 4%, respectively. The resulting reaction mixture

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

Procedure: For example, cyclohexanone oxime gives ε-caprolactam, cycloheptanone oxime gives 7-heptane lactam, cyclooctanone oxime gives 8-octane lactam, and cyclododecanone oxime gives laurolactam

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

Procedure: A solution containing cyclooctanone oxime (9.0 g, 64 mmol) in glacial acetic acid (90 mL) was slowly charged with sodium cyanoborohydride (6.0 g, 95 mmol). The reaction mixture was stirred at ambient temperature for 18 hours then adjusted to pH=9 by the slow addition of cold 2N sodium hydroxide. The resulting precipitate was collected and dried to provide cyclooctyl hydroxylamine as a white solid. The resulting precipitate was collected dried

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

Procedure: A solution containing cyclooctanone (12.6 g, 0.1 mol) and hydroxylamine hydrochloride (14.0 g, 0.2 mole) in a mixture of pyridine (40 mL, 0.5 mole) and ethanol (50 mL) was stirred at ambient temperature for about 15 hours. The solvent was then removed by rotary evaporation. The residue was dissolved in diethyl ether (300 mL) then washed with hydrochloric acid (2×100 mL). The aqueous layer was extracted with diethyl ether (2×150 mL). The ether extracts were combined, dried over magnesium sulfate then concentrated to provide cyclooctanone oxime as a white solid. The solvent was then removed by rotary evaporation The residue was dissolved in diethyl ether (300 mL) then washed with hydrochloric acid (2×100 mL) The aqueous layer was extracted with diethyl ether (2×150 mL) dried over magnesium sulfate then concentrated