3,3-dimethyl-1-(thiolan-1-ium-1-yl)butan-2-one;bromide

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

Procedure: In a 300 ml three-necked flask, 2 g of 2-oxo-3,3-dimethylbutyl-thiacyclopentanium bromide obtained in Example 1 was dissolved in 20 ml of acetonitrile. To the solution, a solution prepared by dissolving 1.69 g of a potassium trifluoromethanesulfonate salt in 50 ml of acetonitrile was added dropwise. After stirring for three hours, the deposited potassium bromide was removed by filtration and acetonitrile was distilled off under reduced pressure by an evaporator. The residue was dissolved in chloroform and the insoluble matter was removed by filtration. Chloroform in the filtrate was distilled off under reduced pressure to obtain a transparent viscous liquid. To the transparent viscous liquid, 5 ml of acetone was added and the solution was added dropwise to 300 ml of diethyl ether. The deposited white crystal was collected by filtration and then recrystallized from ethyl acetate. The resulting white powder was dried under reduced pressure at 30° C. for six hours to obtain 2.21 g of 2-oxo-3,3-dimethylbutyl-thiacyclopentanium trifluoromethanesulfonate (yield: 87.7%). To the solution, a solution prepared was added dropwise the deposited potassium bromide was removed by filtration and acetonitrile was distilled off under reduced pressure by an evaporator The residue was dissolved in chloroform the insoluble matter was removed by filtration Chloroform in the filtrate was distilled off under reduced pressure to obtain a transparent viscous liquid The deposited white crystal was collected by filtration recrystallized from ethyl acetate The resulting white powder was dried under reduced pressure at 30° C. for six hours

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

Procedure: In a 300 ml three-necked flask, 2 g of tetrahydroxythiophene was dissolved in 20 ml of acetone. To the solution, 4.87 g of 1-bromo-3,3-dimethy 2-butanone was added dropwise while stirring. After leaving for 24 hours, the deposited white crystal was collected by filtration. The white crystal was ground to a powder, which was washed with ether. The powder was dried by a vacuum drier at 30° C. for six hours to obtain 5.15 g of 2-oxo-3,3-dimethylbutyl-thiacyclopentanium bromide (yield: 75.0%). After leaving for 24 hours the deposited white crystal was collected by filtration was washed with ether The powder was dried by a vacuum drier at 30° C. for six hours

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

Procedure: In a mixed solvent of 500 ml of water and 100 ml of methanol was dissolved 10 g of potassium perfluorobutanesulfonate, and to the solution was added a solution containing 7.75 g of 2-oxo-3,3-dimethylbutyltetrahydrothiophenium bromide dissolved in 50 ml of methanol. The aqueous solution was extracted twice with each 100 ml of chloroform, and the organic phase was washed with water and concentrated to obtain an oily product. To the oily product was added ethyl acetate, and the solution was again concentrated to obtain a solid product. The solid product was collected by filtration and subjected to reslurry with diisopropyl ether to obtain 9 g of 2-oxo-3,3-dimethylbutyltetrahydrothiophenium perfluorobutanesulfonate. to the solution was added a solution The aqueous solution was extracted twice with each 100 ml of chloroform the organic phase was washed with water concentrated to obtain an oily product the solution was again concentrated to obtain a solid product The solid product was collected by filtration

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

Procedure: In 100 ml of acetonitrile was dissolved 11.8 g of tetrahydrothiophene, to the solution was gradually added 20 g of 1-bromo-3,3-dimethyl-2-butanone. The mixture was stirred at room temperature for 2 days to deposit powder. After adding 100 ml of ethyl acetate to the reaction solution, the powder was collected by filtration, washed with ethyl acetate and dried to obtain 24 g of 2-oxo-3,3-dimethylbutyltetrahydrothiophenium bromide. the powder was collected by filtration washed with ethyl acetate dried

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

Procedure: The synthesis was carried out under radiation from a yellow lamp. The synthesis was similar to the “Synthesis 5” except that the potassium trifluoromethanesulfonate and the 2-oxo-3,3-dimethylbutyl-thiacyclopentanium bromide were replaced with potassium nonafluorobutanesulfonate and 2-oxo-3,3,-dimethylbutyl-thiacyclopentanium bromide, respectively. The present inventors obtained 2-oxo-3,3-dimethylbutyl-thiacyclopentanium nonafluorobutanesulfonate. The yield was 52%, and the melting point was 79.5 degrees in centigrade. The synthesis was carried out under radiation from a yellow lamp

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

Procedure: The synthesis was carried out under radiation from a yellow lamp. The synthesis was similar to the “Synthesis 5” except that the potassium trifluoromethanesulfonate and the 2-oxo-3,3-dimethylbutyl-thiacyclopentanium bromide were replaced with potassium nonafluorobutanesulfonate and 2-oxo-3,3,-dimethylbutyl-thiacyclopentanium bromide, respectively. The present inventors obtained 2-oxo-3,3-dimethylbutyl-thiacyclopentanium nonafluorobutanesulfonate. The yield was 52%, and the melting point was 79.5 degrees in centigrade. The synthesis was carried out under radiation from a yellow lamp

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

Procedure: Using the 100-millilitter 3-port flask, 2 grams of tetrahydrothiophene was dissolved in 20 milli-litter of acetone. 4.87 grams of 1-bromo-3,3-dimethyl-2-butanone was dropped into the solution over agitation. After 24 hours, white crystal was precipitated, and was filtrated. The white crystal was pulverized, and was washed in ether. The pulverized white crystal was dried at 30 degrees in centigrade for 6 hours by using a low-pressure drier. 5.15 grams of 2-oxo-3,3-dimethylbutyl-thiacyclopentanium bromide was obtained. The yield was 75.0%. white crystal was precipitated was filtrated was washed in ether The pulverized white crystal was dried at 30 degrees in centigrade for 6 hours

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

Procedure: 70.2 Parts of tetrahydrothiophene was dissolved in 750 parts of acetone, and 150 parts of 1-bromo-3,3-dimethyl-2-butanone was added dropwise thereto. After the mixture was stirred at room temperature for 24 hours, white solid obtained was filtered, washed with acetone and dried to obtain 161.3 parts of 1-(3,3-dimethyl-2-oxobutyl)tetrahydrothiophenium bromide in the form of white crystals. was added dropwise white solid obtained was filtered washed with acetone dried

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

Procedure: 70.2 Parts of tetrahydrothiophene was dissolved in 750 parts of acetone, and 150 parts of 1-bromo-3,3-dimethyl-2-butanone was added dropwise thereto. After the mixture was stirred at room temperature for 24 hours, white solid obtained was filtered, washed with acetone and dried to obtain 161.3 parts of 1-(3,3-dimethyl-2-oxobutyl)tetrahydrothiophenium bromide in the form of white crystals. was added dropwise white solid obtained was filtered washed with acetone dried

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

Procedure: In a 300 ml three-necked flask, 2 g of 2-oxo-3,3-dimethylbutyl-thiacyclopentanium bromide obtained in Example 1 was dissolved in 20 ml of acetonitrile. To the solution, a solution prepared by dissolving 1.69 g of a potassium trifluoromethanesulfonate salt in 50 ml of acetonitrile was added dropwise. After stirring for three hours, the deposited potassium bromide was removed by filtration and acetonitrile was distilled off under reduced pressure by an evaporator. The residue was dissolved in chloroform and the insoluble matter was removed by filtration. Chloroform in the filtrate was distilled off under reduced pressure to obtain a transparent viscous liquid. To the transparent viscous liquid, 5 ml of acetone was added and the solution was added dropwise to 300 ml of diethyl ether. The deposited white crystal was collected by filtration and then recrystallized from ethyl acetate. The resulting white powder was dried under reduced pressure at 30° C. for six hours to obtain 2.21 g of 2-oxo-3,3-dimethylbutyl-thiacyclopentanium trifluoromethanesulfonate (yield: 87.7%). To the solution, a solution prepared was added dropwise the deposited potassium bromide was removed by filtration and acetonitrile was distilled off under reduced pressure by an evaporator The residue was dissolved in chloroform the insoluble matter was removed by filtration Chloroform in the filtrate was distilled off under reduced pressure to obtain a transparent viscous liquid The deposited white crystal was collected by filtration recrystallized from ethyl acetate The resulting white powder was dried under reduced pressure at 30° C. for six hours

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

Procedure: In a 300 ml three-necked flask, 2 g of 2-oxo-3,3-dimethylbutyl-thiacyclopentanium bromide obtained in Example 1 was dissolved in 20 ml of acetonitrile. To the solution, a solution prepared by dissolving 1.69 g of a potassium trifluoromethanesulfonate salt in 50 ml of acetonitrile was added dropwise. After stirring for three hours, the deposited potassium bromide was removed by filtration and acetonitrile was distilled off under reduced pressure by an evaporator. The residue was dissolved in chloroform and the insoluble matter was removed by filtration. Chloroform in the filtrate was distilled off under reduced pressure to obtain a transparent viscous liquid. To the transparent viscous liquid, 5 ml of acetone was added and the solution was added dropwise to 300 ml of diethyl ether. The deposited white crystal was collected by filtration and then recrystallized from ethyl acetate. The resulting white powder was dried under reduced pressure at 30° C. for six hours to obtain 2.21 g of 2-oxo-3,3-dimethylbutyl-thiacyclopentanium trifluoromethanesulfonate (yield: 87.7%). To the solution, a solution prepared was added dropwise the deposited potassium bromide was removed by filtration and acetonitrile was distilled off under reduced pressure by an evaporator The residue was dissolved in chloroform the insoluble matter was removed by filtration Chloroform in the filtrate was distilled off under reduced pressure to obtain a transparent viscous liquid The deposited white crystal was collected by filtration recrystallized from ethyl acetate The resulting white powder was dried under reduced pressure at 30° C. for six hours

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

Procedure: In a 300 ml three-necked flask, 2 g of tetrahydroxythiophene was dissolved in 20 ml of acetone. To the solution, 4.87 g of 1-bromo-3,3-dimethy 2-butanone was added dropwise while stirring. After leaving for 24 hours, the deposited white crystal was collected by filtration. The white crystal was ground to a powder, which was washed with ether. The powder was dried by a vacuum drier at 30° C. for six hours to obtain 5.15 g of 2-oxo-3,3-dimethylbutyl-thiacyclopentanium bromide (yield: 75.0%). After leaving for 24 hours the deposited white crystal was collected by filtration was washed with ether The powder was dried by a vacuum drier at 30° C. for six hours