tetradecane

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The ethylenolysis of methyl oleate was used as a test to determine the activity of (PCy3)Cl2Ru(3-pentafluorophenyl-6,8-diisopropoxyinden-1-ylidene). A catalyst compound stock solution (0.1379 mM) was made by dissolving the catalyst compound in anhydrous dichloromethane. Methyl oleate (0.87 g, 1.0 mL), catalyst compound stock solution (0.906 g), dichloromethane (4.12 g), and tetradecane (0.152 g) as an internal standard were placed in a Fisher-Porter bottle equipped with a stir bar. The vessel was then filled with ethylene to 150 psig and placed in an oil bath heated to 40° C. for 3 hours. The vessel was then depressurized and 5 drops ethyl vinyl ether added to stop the reaction. A sample was analyzed by gas chromatography. The cross-metathesis reaction yielded 18.5% 1-decene and methyl-9-decenoate with 99% selectivity 1-Decene and methyl-9-decenoate yields corresponded to 4300 turnovers of decene per equivalent of ruthenium. equipped with a stir bar placed in an oil bath the reaction The cross-metathesis reaction

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The ethylenolysis of methyl oleate was used as a test to determine the activity of (PCy3)Cl2Ru(3-pentafluorophenyl-6,8-diisopropoxyinden-1-ylidene). A catalyst compound stock solution (0.1379 mM) was made by dissolving the catalyst compound in anhydrous dichloromethane. Methyl oleate (0.87 g, 1.0 mL), catalyst compound stock solution (0.906 g), dichloromethane (4.12 g), and tetradecane (0.152 g) as an internal standard were placed in a Fisher-Porter bottle equipped with a stir bar. The vessel was then filled with ethylene to 150 psig and placed in an oil bath heated to 40° C. for 3 hours. The vessel was then depressurized and 5 drops ethyl vinyl ether added to stop the reaction. A sample was analyzed by gas chromatography. The cross-metathesis reaction yielded 18.5% 1-decene and methyl-9-decenoate with 99% selectivity 1-Decene and methyl-9-decenoate yields corresponded to 4300 turnovers of decene per equivalent of ruthenium. equipped with a stir bar placed in an oil bath the reaction The cross-metathesis reaction

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The ethylenolysis of methyl oleate was used as a test to determine the activity of (PCy3)Cl2Ru(3-pentafluorophenyl-6,8-diisopropoxyinden-1-ylidene). A catalyst compound stock solution (0.1379 mM) was made by dissolving the catalyst compound in anhydrous dichloromethane. Methyl oleate (0.87 g, 1.0 mL), catalyst compound stock solution (0.906 g), dichloromethane (4.12 g), and tetradecane (0.152 g) as an internal standard were placed in a Fisher-Porter bottle equipped with a stir bar. The vessel was then filled with ethylene to 150 psig and placed in an oil bath heated to 40° C. for 3 hours. The vessel was then depressurized and 5 drops ethyl vinyl ether added to stop the reaction. A sample was analyzed by gas chromatography. The cross-metathesis reaction yielded 18.5% 1-decene and methyl-9-decenoate with 99% selectivity 1-decene and methyl-9-decenoate yields corresponded to 4300 turnovers of decene per equivalent of ruthenium. equipped with a stir bar placed in an oil bath the reaction The cross-metathesis reaction

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The ethylenolysis of methyl oleate was used as a test to determine the activity of (PCy3)Cl2Ru(3-pentafluorophenyl-6,8-diisopropoxyinden-1-ylidene). A catalyst compound stock solution (0.1379 mM) was made by dissolving the catalyst compound in anhydrous dichloromethane. Methyl oleate (0.87 g, 1.0 mL), catalyst compound stock solution (0.906 g), dichloromethane (4.12 g), and tetradecane (0.152 g) as an internal standard were placed in a Fisher-Porter bottle equipped with a stir bar. The vessel was then filled with ethylene to 150 psig and placed in an oil bath heated to 40° C. for 3 hours. The vessel was then depressurized and 5 drops ethyl vinyl ether added to stop the reaction. A sample was analyzed by gas chromatography. The cross-metathesis reaction yielded 18.5% 1-decene and methyl-9-decenoate with 99% selectivity 1-decene and methyl-9-decenoate yields corresponded to 4300 turnovers of decene per equivalent of ruthenium. equipped with a stir bar placed in an oil bath the reaction The cross-metathesis reaction

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The ethylenolysis of methyl oleate was used as a test to determine the activity of (PCy3)Cl2Ru(3-pentafluorophenyl-6,8-diisopropoxyinden-1-ylidene). A catalyst compound stock solution (0.1379 mM) was made by dissolving the catalyst compound in anhydrous dichloromethane. Methyl oleate (0.87 g, 1.0 mL), catalyst compound stock solution (0.906 g), dichloromethane (4.12 g), and tetradecane (0.152 g) as an internal standard were placed in a Fisher-Porter bottle equipped with a stir bar. The vessel was then filled with ethylene to 150 psig and placed in an oil bath heated to 40° C. for 3 hours. The vessel was then depressurized and 5 drops ethyl vinyl ether added to stop the reaction. A sample was analyzed by gas chromatography. The cross-metathesis reaction yielded 18.5% 1-decene and methyl-9-decenoate with 99% selectivity 1-decene and methyl-9-decenoate yields corresponded to 4300 turnovers of decene per equivalent of ruthenium. equipped with a stir bar placed in an oil bath the reaction The cross-metathesis reaction

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

Procedure: A mixture of 730 mg 2,8-dimethyl-1-oxa-8-azaspiro[4,5]decan-3-one, 2.25 ml ethylene glycol, 836 mg p-toluenesulfonic acid monohydrate and 30 ml toluene was heated under reflux for 3 hours with a Dean-Strak azeotropic dehydration apparatus, and the reaction mixture was poured into 30 ml of an aqueous solution containing 1.26 g sodium becarbonate, the resulting mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography on silica gel eluted with a mixted solvent of chloroform/methanol/conc. ammonia (20:1:0.1 by volume) to give 640 mg of 10,14-dimethyl-1,4, 13-trioxa-10-azasprio[4.1.5.2]tetradecane as oil. It was dissolved in isopropanol, and a solution of maleic acid in isopropanol was added to convert it to the corresponding maleate, which was recrystallized from dichloromethane/ether. was heated under reflux for 3 hours with a Dean-Strak azeotropic dehydration apparatus the resulting mixture was extracted with chloroform The extract was dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography on silica gel eluted with a mixted solvent of chloroform/methanol/conc

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

Procedure: A mixture of 730 mg 2,8-dimethyl-1-oxa-8-azaspiro[4,5]-decan-3-one, 2.25 ml ethylene glycol, 836 mg p-toluenesulfonic acid monohydrate and 30 ml toluene was heated under reflux for 3 hours with a Dean-Strak azeotropic dehydration apparatus, and the reaction mixture was poured into 30 ml of an aqueous solution containing 1.26 g sodium becarbonate. The resulting mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography on silica gel eluted with a mixted solvent of chloroform/methanol/conc. ammonia (20:1:0.1 by volume) to give 640 mg of 10,14-dimethyl-1,4, 13-trioxa-10-azasprio[4.1.5.2]tetradecane as oil. It was dissolved in isopropanol, and a solution of maleic acid in isopropanol was added to convert it to the corresponding maleate, which was recrystallized from dichloromethane/ether. was heated under reflux for 3 hours with a Dean-Strak azeotropic dehydration apparatus The resulting mixture was extracted with chloroform The extract was dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography on silica gel eluted with a mixted solvent of chloroform/methanol/conc

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

Procedure: In a reaction vessel the mixture of 2 ml (5.9 mmol) of methyl oleate, the corresponding amount of 2-butene-1,4-diol (1.46 ml or 2.43 ml), 0.2 ml of tetradecane (internal standard) and 2 ml of the corresponding solvent is prepared and shaken. Thereafter a blank sample is taken for GC measurement. After sampling has taken place, the corresponding catalyst (2 mol %) is added and the reaction vessel is placed in the temperature-conditioned carousel reactor. The mixture is heated for 4 hours and stirring is continued, and after that the final GC sample is taken for kinetic determinations. After 4 hours the reaction is halted by addition of 2 ml of ethyl vinyl ether. After sampling the corresponding catalyst (2 mol %) is added The mixture is heated for 4 hours stirring

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 278 μL (2 mmol) 1-bromonaphthaline, 20 mg (0.2 mmol) copper(I) chloride, 550 mg (4 mmol) potassium carbonate, 260 mg (2.4 mmol) o-cresol, 130 μL 1-butylimidazole, 2 mL toluene and 200 μL internal standard (tetradecane) were added to an Ace pressure tube under argon and heated to 120° C. for 16 h. After cooling, water and diethyl ether were added, the organic phase was washed with 10% K2CO3 solution, water and brine and dried over Na2SO4. GC analysis of the organic phase showed a yield of 89%. After evaporation of the solvents, the dark brown oil was submitted to column chromatography over silica gel, eluent light petroleum. 0.38 g of colourless oil was recovered (81% isolated yield). The substance was identified by gc/ms and nmr spectroscopy. After cooling the organic phase was washed with 10% K2CO3 solution, water and brine dried over Na2SO4 After evaporation of the solvents 0.38 g of colourless oil was recovered (81% isolated yield)

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

Procedure: A solution of diols from Example 1d (3.0 g, ˜6.5 mmol of the main diastereomeric pair of enantiomers of 5a), 2,2-dimethoxypropane (4.0 g, 0.38 mol) lithium bromide (0.1 g) and p-toluenesulfonic acid (0.1 g) in THF (40 ml) was stirred at r. t. for 2 h, then poured onto saturated aqueous sodium bicarbonate solution (100 ml) and extracted with MTBE (2×100 ml). The combined organic phases were washed with water (2×100 ml), dried (Na2SO4), concentrated in vacuo and the residue (3.0 g) purified by flash chromatography (MTBE/hexane 1:20) to afford a mixture of isomeric diols (0.60 g, colourless oil) in which the main diastereoisomeric pair of enantiomers of 2,2,6,6,10,10-hexamethyl-5,7-dioxatetracyclo[9.2.1.01.9, 04.8]tetradecane (Ia) constituted 73% (24% yield). extracted with MTBE (2×100 ml) The combined organic phases were washed with water (2×100 ml) dried (Na2SO4) concentrated in vacuo the residue (3.0 g) purified by flash chromatography (MTBE/hexane 1:20) to afford

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

Procedure: A mixture of 730 mg 2,8-dimethyl-1-oxa-8-azaspiro[4,5]-decan-3-one, 2.25 ml ethylene glycol, 836 mg p-toluenesulfonic acid monohydrate and 30 ml toluene was heated under reflux for 3 hours with a Dean-Strak azeotropic dehydration apparatus, and the reaction mixture was poured into 30 ml of an aqueous solution containing 1.26 g sodium becarbonate. The resulting mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography on silica gel eluted with a mixted solvent of chloroform/methanol/conc. ammonia (20:1:0.1 by volume) to give 640 mg of 10,14-dimethyl-1,4, 13-trioxa-10-azasprio[4.1.5.2]tetradecane as oil. It was dissolved in isopropanol, and a solution of maleic acid in isopropanol was added to convert it to the corresponding maleate, which was recrystallized from dichloromethane/ether. was heated under reflux for 3 hours with a Dean-Strak azeotropic dehydration apparatus The resulting mixture was extracted with chloroform The extract was dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography on silica gel eluted with a mixted solvent of chloroform/methanol/conc

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

Procedure: In a reaction vessel the mixture of 2 ml (5.9 mmol) of methyl oleate, the corresponding amount of 2-butene-1,4-diol (1.46 ml or 2.43 ml), 0.2 ml of tetradecane (internal standard) and 2 ml of the corresponding solvent is prepared and shaken. Thereafter a blank sample is taken for GC measurement. After sampling has taken place, the corresponding catalyst (2 mol %) is added and the reaction vessel is placed in the temperature-conditioned carousel reactor. The mixture is heated for 4 hours and stirring is continued, and after that the final GC sample is taken for kinetic determinations. After 4 hours the reaction is halted by addition of 2 ml of ethyl vinyl ether. After sampling the corresponding catalyst (2 mol %) is added The mixture is heated for 4 hours stirring