4-ethenylcyclohexene

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

Procedure: 13.1 g of the catayst prepared in Example 17 was charged into a steel reactor under a blanket of nitrogen. To this was added 8.4 g of 1,2-dicyclohex-4-enyl ethylene and 27 g of isobutene. The reactor was sealed and rocked. After 1 hour at ambient temperature, the products were analysed. 3.7% of the 1,2-dicyclohex-4-vinyl ethylene was converted affording dismutation products with the following selectivities 31.3% 4-isobutenylcyclohexene and 69.% 4-vinylcyclohexene. 13.1 g of the catayst prepared in Example 17 was charged into a steel reactor under a blanket of nitrogen The reactor was sealed

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

Procedure: 13.1 g of the catayst prepared in Example 17 was charged into a steel reactor under a blanket of nitrogen. To this was added 8.4 g of 1,2-dicyclohex-4-enyl ethylene and 27 g of isobutene. The reactor was sealed and rocked. After 1 hour at ambient temperature, the products were analysed. 3.7% of the 1,2-dicyclohex-4-vinyl ethylene was converted affording dismutation products with the following selectivities 31.3% 4-isobutenylcyclohexene and 69.% 4-vinylcyclohexene. 13.1 g of the catayst prepared in Example 17 was charged into a steel reactor under a blanket of nitrogen The reactor was sealed

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

Procedure: The process of Example 18 was repeated except that the catalyst was impregnated with tetramethyltin before use and the feed was 27 g of isobutene and 9.6 g of 1,2-dicyclohex-4-enylethene. The catalyst so prepared contained 6.4% by weight SnMe4. After 30 minutes reaction the products were analysed. 13.7% of the 1,2-dicyclohex-4-enylethylene was converted affording dismutation products with the following seectivities 54% 4-isobutenylcyclohexene and 4.6% 4-vinylcylohexene. The catalyst so prepared After 30 minutes reaction the products

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a control run, the following reaction mixture was prepared in a Fisher-Porter aerosol compatibility bottle: 0.25 grams (1.5 mmol) of ferric chloride, 0.3 grams (2.5 mg-atom) of tin powder and 0.3 grams (4.5 mmol) of sodium nitrite. The bottle reactor was evacuated then flushed with nitrogen followed by the addition of 10 ml of THF. The mixture was cooled with dry ice and 18.3 grams (339 mmol) of 1,3-butadiene added. This reaction mixture was heated to 75° C. with stirring. During this time, the original dark green solution changed in color to an orange-brown color. After 5 hours, the reaction was terminated and the reaction mixture allowed to cool to room temperature and stand for 1 day. Pressure on the reactor was still at 25 psig indicating there had been little, if any, conversion of 1,3-butadiene to the dimer. The results of this run indicate that one does not obtain dimerization of 1,3-butadiene to 4-vinylcyclohexene if one attempts to form the iron nitrosyl halide simultaneously with the dimerization. In a control run, the following reaction mixture was prepared in a Fisher-Porter aerosol compatibility bottle The bottle reactor was evacuated then flushed with nitrogen followed by the addition of 10 ml of THF added the reaction was terminated to cool to room temperature stand for 1 day The results of this run

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a control run, the following reaction mixture was prepared in a Fisher-Porter aerosol compatibility bottle: 0.25 grams (1.5 mmol) of ferric chloride, 0.3 grams (2.5 mg-atom) of tin powder and 0.3 grams (4.5 mmol) of sodium nitrite. The bottle reactor was evacuated then flushed with nitrogen followed by the addition of 10 ml of THF. The mixture was cooled with dry ice and 18.3 grams (339 mmol) of 1,3-butadiene added. This reaction mixture was heated to 75° C. with stirring. During this time, the original dark green solution changed in color to an orange-brown color. After 5 hours, the reaction was terminated and the reaction mixture allowed to cool to room temperature and stand for 1 day. Pressure on the reactor was still at 25 psig indicating there had been little, if any, conversion of 1,3-butadiene to the dimer. The results of this run indicate that one does not obtain dimerization of 1,3-butadiene to 4-vinylcyclohexene if one attempts to form the iron nitrosyl halide simultaneously with the dimerization. In a control run, the following reaction mixture was prepared in a Fisher-Porter aerosol compatibility bottle The bottle reactor was evacuated then flushed with nitrogen followed by the addition of 10 ml of THF added the reaction was terminated to cool to room temperature stand for 1 day The results of this run

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a control run, the following reaction mixture was prepared in a Fisher-Porter aerosol compatibility bottle: 0.25 grams (1.5 mmol) of ferric chloride, 0.3 grams (2.5 mg-atom) of tin powder and 0.3 grams (4.5 mmol) of sodium nitrite. The bottle reactor was evacuated then flushed with nitrogen followed by the addition of 10 ml of THF. The mixture was cooled with dry ice and 18.3 grams (339 mmol) of 1,3-butadiene added. This reaction mixture was heated to 75° C. with stirring. During this time, the original dark green solution changed in color to an orange-brown color. After 5 hours, the reaction was terminated and the reaction mixture allowed to cool to room temperature and stand for 1 day. Pressure on the reactor was still at 25 psig indicating there had been little, if any, conversion of 1,3-butadiene to the dimer. The results of this run indicate that one does not obtain dimerization of 1,3-butadiene to 4-vinylcyclohexene if one attempts to form the iron nitrosyl halide simultaneously with the dimerization. In a control run, the following reaction mixture was prepared in a Fisher-Porter aerosol compatibility bottle The bottle reactor was evacuated then flushed with nitrogen followed by the addition of 10 ml of THF added the reaction was terminated to cool to room temperature stand for 1 day The results of this run

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

Procedure: Using the same apparatus and procedure described in EXAMPLE 1, 37.8 g (0.35 mol) of 4-vinylcyclohexene and 60 μl of 1% chloroplatinic acid in isopropanol were added to the flask. Through the dropping funnel was added dropwise 10.0 g (0.07 mmol) of allyldichlorosilane for 30 min at 80° C. and the solution was further reacted for 3 hrs to complete the reaction. Vacuum distillation (70-73° C./0.5 torr) of the product mixture gave 13.5 g (78%) of 6-(3-hexenyl)-4,4-dichloro-4-sila-1-hexene. were added to the flask the solution was further reacted for 3 hrs the reaction Vacuum distillation (70-73° C./0.5 torr) of the product mixture

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a control run, the following reaction mixture was prepared in a Fisher-Porter aerosol compatibility bottle: 0.25 grams (1.5 mmol) of ferric chloride, 0.3 grams (2.5 mg-atom) of tin powder and 0.3 grams (4.5 mmol) of sodium nitrite. The bottle reactor was evacuated then flushed with nitrogen followed by the addition of 10 ml of THF. The mixture was cooled with dry ice and 18.3 grams (339 mmol) of 1,3-butadiene added. This reaction mixture was heated to 75° C. with stirring. During this time, the original dark green solution changed in color to an orange-brown color. After 5 hours, the reaction was terminated and the reaction mixture allowed to cool to room temperature and stand for 1 day. Pressure on the reactor was still at 25 psig indicating there had been little, if any, conversion of 1,3-butadiene to the dimer. The results of this run indicate that one does not obtain dimerization of 1,3-butadiene to 4-vinylcyclohexene if one attempts to form the iron nitrosyl halide simultaneously with the dimerization. In a control run, the following reaction mixture was prepared in a Fisher-Porter aerosol compatibility bottle The bottle reactor was evacuated then flushed with nitrogen followed by the addition of 10 ml of THF added the reaction was terminated to cool to room temperature stand for 1 day The results of this run

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

Procedure: Using the same apparatus and procedure described in EXAMPLE 1, 37.8 g (0.35 mol) of 4-vinylcyclohexene and 60 μl of 1% chloroplatinic acid in isopropanol were added to the flask. Through the dropping funnel was added dropwise 10.0 g (0.07 mmol) of allyldichlorosilane for 30 min at 80° C. and the solution was further reacted for 3 hrs to complete the reaction. Vacuum distillation (70-73° C./0.5 torr) of the product mixture gave 13.5 g (78%) of 6-(3-hexenyl)-4,4-dichloro-4-sila-1-hexene. were added to the flask the solution was further reacted for 3 hrs the reaction Vacuum distillation (70-73° C./0.5 torr) of the product mixture

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

Procedure: Dicyclopentadiene and 4-vinylcyclohexene in equimolar mixture were heated in an autoclave at 240° C. for 4-4.5 hours. The reaction product was diluted with cyclohexane and passed through a packed bed of alumina to remove the t-butyl-catechol inhibitor introduced with the reactants. The resulting product mixture was distilled in a wiped film evaporator at 3 mm Hg pressure at 90° C. to produce a light fraction containing unreacted vinylcyclohexene and dicyclopentadiene and the mono-adducts of 4-vinylcyclohexene and cyclo-pentadiene. A 150g sample of this distillate was vacuum distilled using a 10-tray Oldershaw column to give four fractions. The fourth fraction, 65g, was shown by gas chromatographic analysis to consist of 0.15% dicyclopentadiene, 88.3% endo-5-(3-cyclohexen-1-yl)-2-norbornene, 6.1% exo-5-(3-cyclohexen-1-yl)-2-norbornene and two additional components present in the amount of 1.9% and 2.4% which are believed to be isomeric adducts of the formula ##STR9## several additional components totalling about 0.4%, 0.4% tricyclopentadiene and about 0.4% unidentified components. Analysis of the fraction by nuclear magnetic resonance indicated about 87 mole percent of the endo adduct, about 9 mole percent of the exo adduct and about 5% of the isomeric adducts. to remove the t-butyl-catechol inhibitor introduced with the reactants The resulting product mixture was distilled in a wiped film evaporator at 3 mm Hg pressure at 90° C. to produce a light fraction distilled to give four fractions

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

Procedure: Dicyclopentadiene and 4-vinylcyclohexene in equimolar mixture were heated in an autoclave at 240° C. for 4-4.5 hours. The reaction product was diluted with cyclohexane and passed through a packed bed of alumina to remove the t-butyl-catechol inhibitor introduced with the reactants. The resulting product mixture was distilled in a wiped film evaporator at 3 mm Hg pressure at 90° C. to produce a light fraction containing unreacted vinylcyclohexene and dicyclopentadiene and the mono-adducts of 4-vinylcyclohexene and cyclo-pentadiene. A 150g sample of this distillate was vacuum distilled using a 10-tray Oldershaw column to give four fractions. The fourth fraction, 65g, was shown by gas chromatographic analysis to consist of 0.15% dicyclopentadiene, 88.3% endo-5-(3-cyclohexen-1-yl)-2-norbornene, 6.1% exo-5-(3-cyclohexen-1-yl)-2-norbornene and two additional components present in the amount of 1.9% and 2.4% which are believed to be isomeric adducts of the formula ##STR9## several additional components totalling about 0.4%, 0.4% tricyclopentadiene and about 0.4% unidentified components. Analysis of the fraction by nuclear magnetic resonance indicated about 87 mole percent of the endo adduct, about 9 mole percent of the exo adduct and about 5% of the isomeric adducts. to remove the t-butyl-catechol inhibitor introduced with the reactants The resulting product mixture was distilled in a wiped film evaporator at 3 mm Hg pressure at 90° C. to produce a light fraction distilled to give four fractions

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

Procedure: Dicyclopentadiene and 4-vinylcyclohexene in equimolar mixture were heated in an autoclave at 240° C. for 4-4.5 hours. The reaction product was diluted with cyclohexane and passed through a packed bed of alumina to remove the t-butyl-catechol inhibitor introduced with the reactants. The resulting product mixture was distilled in a wiped film evaporator at 3 mm Hg pressure at 90° C. to produce a light fraction containing unreacted vinylcyclohexene and dicyclopentadiene and the mono-adducts of 4-vinylcyclohexene and cyclo-pentadiene. A 150g sample of this distillate was vacuum distilled using a 10-tray Oldershaw column to give four fractions. The fourth fraction, 65g, was shown by gas chromatographic analysis to consist of 0.15% dicyclopentadiene, 88.3% endo-5-(3-cyclohexen-1-yl)-2-norbornene, 6.1% exo-5-(3-cyclohexen-1-yl)-2-norbornene and two additional components present in the amount of 1.9% and 2.4% which are believed to be isomeric adducts of the formula ##STR9## several additional components totalling about 0.4%, 0.4% tricyclopentadiene and about 0.4% unidentified components. Analysis of the fraction by nuclear magnetic resonance indicated about 87 mole percent of the endo adduct, about 9 mole percent of the exo adduct and about 5% of the isomeric adducts. to remove the t-butyl-catechol inhibitor introduced with the reactants The resulting product mixture was distilled in a wiped film evaporator at 3 mm Hg pressure at 90° C. to produce a light fraction distilled to give four fractions