1-(chloromethyl)-3-ethenylbenzene

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

Procedure: A polymerization inhibitor, p-methoxyphenol (1.24 g; 0.01 mole), was added to a mixture of 78 g (1.0 mole) of 2-mercaptoethanol, 133 g (1.0 mole) of a 30 % aqueous solution of sodium hydroxide and 0.15 liter of methanol. While the mixture was cooled to below 10° C., 152 g (1.0 mole) of m-(chloromethyl)styrene was added dropwise over 3 hours. Then, the reaction mixture was continuously stirred for an additional 3 hours to complete the reaction. Water (1 liter) was added to the reaction mixture to separate it into an oil layer and an aqueous layer. The oil layer was washed with water and distilled under reduced pressure (140°-150 ° C./1-2 mmHg) to give 105 g of 2-(3-vinylbenzylthio)ethanol as a colorless transparent liquid. While the mixture was cooled to below 10° C. the reaction to separate it into an oil layer The oil layer was washed with water distilled under reduced pressure (140°-150 ° C./1-2 mmHg)

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

Procedure: A polymerization inhibitor, p-methoxyphenol (1.24 g; 0.01 mole), was added to a mixture of 78 g (1.0 mole) of 2-mercaptoethanol, 133 g (1.0 mole) of a 30 % aqueous solution of sodium hydroxide and 0.15 liter of methanol. While the mixture was cooled to below 10° C., 152 g (1.0 mole) of m-(chloromethyl)styrene was added dropwise over 3 hours. Then, the reaction mixture was continuously stirred for an additional 3 hours to complete the reaction. Water (1 liter) was added to the reaction mixture to separate it into an oil layer and an aqueous layer. The oil layer was washed with water and distilled under reduced pressure (140°-150 ° C./1-2 mmHg) to give 105 g of 2-(3-vinylbenzylthio)ethanol as a colorless transparent liquid. While the mixture was cooled to below 10° C. the reaction to separate it into an oil layer The oil layer was washed with water distilled under reduced pressure (140°-150 ° C./1-2 mmHg)

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

Procedure: 3-Ethenylbenzyl alcohol (5.26 g) was dissolved in carbon tetrachloride (100 ml) and triphenylphosphine (10.2 g) added. The solution was refluxed overnight and then left to cool. A white precipitate formed which was filtered through celite. The filtrate was evaporated in vacuo to yield a crude product. The residue was purified by gravity chromatography on silica using 5% dichloromethane in petrol (60-80) as eluant. This yielded the pure product. The solution was refluxed overnight left to cool A white precipitate formed which was filtered through celite The filtrate was evaporated in vacuo

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

Procedure: 3-Ethenylbenzyl alcohol (5.26 g) was dissolved in carbon tetrachloride (100 ml) and triphenylphosphine (10.2 g) added. The solution was refluxed overnight and then left to cool. A white precipitate formed which was filtered through celite. The filtrate was evaporated in vacuo to yield a crude product. The residue was purified by gravity chromatography on silica using 5% dichloromethane in petrol (60-80) as eluant. This yielded the pure product. The solution was refluxed overnight left to cool A white precipitate formed which was filtered through celite The filtrate was evaporated in vacuo

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

Procedure: The title compound was prepared in a manner analogous to Example 1. The components were ar-vinyl-benzyl chloride (approximately 95% para isomer, 0.249 mol.), potassium carbonate (50.0 g.), anhydrous methanol (1000 ml.) and 2-methylaziridine (70 ml.; 0.974 mol.). Distillation of the crude product (a brown oil) gave 7.6 g. of a water-white liquid boiling at about 85°C. under 0.2-0.3 mm. of Hg pressure. VPC analysis showed this fraction to contain 87.1% of the desired product. The product was obtained from the VPC fractionation and its structure confirmed by IR, NMR and elemental analysis. The title compound was prepared in a manner analogous to Example 1 Distillation of the crude product (a brown oil) gave 7.6 g The product was obtained from the VPC fractionation and its structure

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

Procedure: To a 1-liter, 3-necked flask equipped with a mechanical stirrer, reflux condenser and dropping funnel was charged 86 g. (2.0 mole) of aziridine, 66 g. of 85% powdered KOH (1.0 mole) and 400 ml. of benzene. The mixture was stirred and heated to reflux and 76.25 g. (0.5 mole) of ar-vinylbenzyl chloride containing 0.1% by weight of p,p'-diphenylphenylene diamine inhibitor was added over 15 minutes. The ar-vinylbenzyl chloride was an isomeric mixture consisting of approximately 60-70% meta isomer and 40-30% para isomer. The reaction mixture was then stirred rapidly under reflux for four hours, cooled to room temperature, filtered through a filter cell and the filtrate concentrated at reduced pressure to give 72.4 g. (91.1%) of crude product. This crude product was distilled at reduced pressure to give 63.1 g. (79.4%) of water-white N-ar-vinylbenzylaziridine b.p. 72°-73°/0.6 mm. whose identity was established by IR and NMR. Its purity was found to be greater than 99% by vapor phase chromatography on a G.E. silicone column (10 ft. × 1/4 in.) at 200° C. and 60 ml./min. helium flow rate. To a 1-liter, 3-necked flask equipped with a mechanical stirrer reflux condenser was charged 86 g heated to reflux The reaction mixture was then stirred rapidly under reflux for four hours filtered through a filter cell the filtrate concentrated at reduced pressure to give 72.4 g This crude product was distilled at reduced pressure to give 63.1 g at 200° C.

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

Procedure: Anhydrous methanol (200 ml.), anhydrous potassium carbonate (10.0 g.) and ar-vinylbenzyl chloride (approximately 95% para isomer; 0.05 mol.) were charged to a predried reaction vessel equipped with a stirring means and a drying tube. Aziridine (27.0 ml.; 0.5 mol.) was added dropwise to the stirred reaction mixture. Subsequently, the stirred mixture was maintained at room temperature for 24 hours. The work up comprised adding a diatomaceous earth filtering aid to the reaction mixture, filtering out the solids, removing the solvent from the filtrate under reduced pressure and recovering as the pot residue 7.7 g. of crude product as a yellow/orange liquid. The product was purified by distillative techniques under reduced pressure. The product was thus obtained as a water-white liquid boiling at 50°-52°C. at 0.15-0.20 mm. of Hg pressure. Vapor phase chromatography (VPC) of this fraction showed it to contain 85.7% of the desired product. The compound was obtained from the VPC fractionation and its structure confirmed by infrared (IR) analysis, nuclear magnetic resonance (NMR) and elemental analysis. equipped with a stirring means and a drying tube The work up comprised adding a diatomaceous earth filtering aid to the reaction mixture filtering out the solids removing the solvent from the filtrate under reduced pressure recovering as the pot residue 7.7 g The product was purified by distillative techniques under reduced pressure The product was thus obtained as a water-white liquid boiling at 50°-52°C. at 0.15-0.20 mm. of Hg pressure

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

Procedure: A polymerization inhibitor, p-methoxyphenol (1.24 g; 0.01 mole), was added to a mixture of 78 g (1.0 mole) of 2-mercaptoethanol, 133 g (1.0 mole) of a 30 % aqueous solution of sodium hydroxide and 0.15 liter of methanol. While the mixture was cooled to below 10° C., 152 g (1.0 mole) of m-(chloromethyl)styrene was added dropwise over 3 hours. Then, the reaction mixture was continuously stirred for an additional 3 hours to complete the reaction. Water (1 liter) was added to the reaction mixture to separate it into an oil layer and an aqueous layer. The oil layer was washed with water and distilled under reduced pressure (140°-150 ° C./1-2 mmHg) to give 105 g of 2-(3-vinylbenzylthio)ethanol as a colorless transparent liquid. While the mixture was cooled to below 10° C. the reaction to separate it into an oil layer The oil layer was washed with water distilled under reduced pressure (140°-150 ° C./1-2 mmHg)

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

Procedure: 3-Ethenylbenzyl alcohol (5.26 g) was dissolved in carbon tetrachloride (100 ml) and triphenylphosphine (10.2 g) added. The solution was refluxed overnight and then left to cool. A white precipitate formed which was filtered through celite. The filtrate was evaporated in vacuo to yield a crude product. The residue was purified by gravity chromatography on silica using 5% dichloromethane in petrol (60-80) as eluant. This yielded the pure product. The solution was refluxed overnight left to cool A white precipitate formed which was filtered through celite The filtrate was evaporated in vacuo