adamantane-1,3,5-triol

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

Procedure: This 1,3,5-trihydroxyadamantane was dissolved in methylene chloride. To this solution were added a small amount of trimethylamine, and then an equimolar amount of trimethylsilyl chloride. Reaction was carried out at room temperature. The reaction product was partitioned by high performance liquid chromatography to obtain 1,3-dihydroxy-5-trimethylsiloxyadamantane. Reaction was carried out at room temperature The reaction product was partitioned by high performance liquid chromatography

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

Procedure: One mol of 1,3-dihydroxyadamantane was stirred in an acetic acid-acetic anhydride solution of CrO3, oxidizing agent, with heating. After carrying out the reaction for 8 hours, the reaction solution was neutralized to obtain a mixture of polyhydroxylated compounds of hydroxyadamantane. This mixture was partitioned by high performance liquid chromatography to obtain 1,3,5-trihydroxyadamantane. with heating the reaction for 8 hours to obtain This mixture was partitioned by high performance liquid chromatography

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (6.7 mg, 0.01 mmol) and sodium carbonate (64 mg, 0.6 mmol) in toluene (1.0 ml), 1,3,5-adamantanetriol (1 mmol) and vinyl acetate (9 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 5 hours. The reaction mixture was analyzed by gas chromatography to find that 1,3,5-tris(vinyloxy)adamantane, 3,5-bis(vinyloxy)-1-adamantanol, and 5-vinyloxy-1,3-adamantanediol were produced in yields of 52%, 18%, and 8%, respectively, with a conversion from 1,3,5-adamantanetriol of 97%. were added

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 92.12 g (0.5 mol) of 1,3,5-adamantanetriol are suspended in 153.14 g (1.5 mol) of acetic anhydride. Subsequently, 10 drops of concentrated sulfuric acid are added and the mixture is stirred on a rotary evaporator (without vacuum) until a homogeneous solution has formed. Subsequently, the mixture is heated to 100° C. under reflux for 2 h. After cooling, the reaction mixture is added to 300 ml of ice-water and extracted with dichloromethane. The combined organic phases are deacidified with sodium carbonate solution and washed with water. The mixture is dried over magnesium sulfate and filtered, and the solvent is removed under reduced pressure. 150.50 g (0.48 mol; 97.0%) of a colorless oil are obtained. has formed under reflux for 2 h After cooling extracted with dichloromethane washed with water The mixture is dried over magnesium sulfate filtered the solvent is removed under reduced pressure 150.50 g (0.48 mol; 97.0%) of a colorless oil are obtained

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.68 grams (10 millimoles) of 1,3-adamantanediol, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide, 0.015 gram (0.06 millimole) of Co(AA)2 and 25 milliliters of acetic acid was stirred under an oxygen atmosphere at a temperature of 95° C. for 6 hours. Thus, 1,3-adamantanediol was transformed, with a transformation rate of 99%, into 1,3,5-adamantanetriol (selectivity for 1,3-adamantanediol 37%, yield 37%) and 1,3,5,7-adamantanetetraol (selectivity for 1,3-adamantanediol 62%, yield 62%). The selectivity for the alcohols was 99%.

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

Procedure: To 25 milliliters of acetic acid were added 1.52 grams (10 millimoles) of 1-adamantanol, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide and 0.015 gram (0.06 millimole) of Co(AA)2, and the resultant mixture was stirred under an oxygen atmosphere at a temperature of 75° C. for three hours. As a result, 1-adamantanol was transformed, with a transformation rate of 80%, into 1,3-adamantanediol (selectivity for 1-adamantanol 66%, yield 53%) and 1,3,5-adamantanetriol (selectivity for 1-adamantanol 33%, yield 26%), with a selectivity for the alcohols of 99%.

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

Procedure: To 25 milliliters of acetic acid were added 1.52 grams (10 millimoles) of 1-adamantanol, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide and 0.015 gram (0.06 millimole) of Co(AA)2, and the resultant mixture was stirred under an oxygen atmosphere at a temperature of 75° C. for three hours. As a result, 1-adamantanol was transformed, with a transformation rate of 80%, into 1,3-adamantanediol (selectivity for 1-adamantanol 66%, yield 53%) and 1,3,5-adamantanetriol (selectivity for 1-adamantanol 33%, yield 26%), with a selectivity for the alcohols of 99%.

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

Procedure: This 1,3,5-trihydroxyadamantane was dissolved in methylene chloride. To this solution were added a small amount of trimethylamine, and then an equimolar amount of trimethylsilyl chloride. Reaction was carried out at room temperature. The reaction product was partitioned by high performance liquid chromatography to obtain 1,3-dihydroxy-5-trimethylsiloxyadamantane. Reaction was carried out at room temperature The reaction product was partitioned by high performance liquid chromatography

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

Procedure: This 1,3,5-trihydroxyadamantane was dissolved in methylene chloride. To this solution were added a small amount of trimethylamine, and then an equimolar amount of trimethylsilyl chloride. Reaction was carried out at room temperature. The reaction product was partitioned by high performance liquid chromatography to obtain 1,3-dihydroxy-5-trimethylsiloxyadamantane. Reaction was carried out at room temperature The reaction product was partitioned by high performance liquid chromatography

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

Procedure: One mol of 1,3-dihydroxyadamantane was stirred in an acetic acid-acetic anhydride solution of CrO3, oxidizing agent, with heating. After carrying out the reaction for 8 hours, the reaction solution was neutralized to obtain a mixture of polyhydroxylated compounds of hydroxyadamantane. This mixture was partitioned by high performance liquid chromatography to obtain 1,3,5-trihydroxyadamantane. with heating the reaction for 8 hours to obtain This mixture was partitioned by high performance liquid chromatography

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

Procedure: This 1,3,5-trihydroxyadamantane was dissolved in methylene chloride. To this solution were added a small amount of trimethylamine, and then an equimolar amount of trimethylsilyl chloride. Reaction was carried out at room temperature. The reaction product was partitioned by high performance liquid chromatography to obtain 1,3-dihydroxy-5-trimethylsiloxyadamantane. Reaction was carried out at room temperature The reaction product was partitioned by high performance liquid chromatography

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

Procedure: One mol of 1,3-dihydroxyadamantane was stirred in an acetic acid-acetic anhydride solution of CrO3, oxidizing agent, with heating. After carrying out the reaction for 8 hours, the reaction solution was neutralized to obtain a mixture of polyhydroxylated compounds of hydroxyadamantane. This mixture was partitioned by high performance liquid chromatography to obtain 1,3,5-trihydroxyadamantane. with heating the reaction for 8 hours to obtain This mixture was partitioned by high performance liquid chromatography