benzenesulfinyl chloride

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The diene (2) is treated with a halogenating agent such as phenylselenyl chloride or bromide or phenylsulfinyl chloride, preferably phenylselenyl chloride, in an approximately equimolar ratio in an inert solvent at about -80° C., for approximately 20 minutes; illustrative of such inert solvents are methylene chloride, ether and the like. After a standard workup the product residue is dissolved in an ethereal solvent, chilled to about 0° C. and oxidized with an agent such as 30% hydrogen peroxide or a peroxy acid such as peroxybenzoic acid to yield a halohydrin analog (3). After a standard workup the product residue is dissolved in an ethereal solvent

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

Procedure: Benzenesulphinamide was prepared by reacting benzenesulphinyl chloride with ammonia in ether initially at -78° C. and finally at ambient temperature and was isolated in 17% yield as a solid, m.p. 112°-115° C. initially at -78° C. finally at ambient temperature and was isolated in 17% yield as a solid, m.p. 112°-115° C.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a general description of scheme 1 the diene (2) of step (A) is treated with a halogenating agent such as phenylselenyl chloride or bromide or phenylsulfinyl chloride, preferably phenylselenyl chloride, in an approximately equimolar ratio in an inert solvent at about -80° C., for approximately 20 minutes; illustrative of such inert solvents are methylene chloride, ether and the like. After a standard workup the product residue is dissolved in an ethereal solvent, chilled to about 0° C. and oxidized with an agent such as 30% hydrogen peroxide or a peroxy acid such as peroxybenzoic acid to yield a halohydrin analog (1-3). After a standard workup the product residue is dissolved in an ethereal solvent

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The diene (2) of step (B) is treated with a halogenating agent such as phenylselenyl chloride or bromide or phenylsulfinyl chloride, preferably phenylselenyl chloride, in an approximately equimolar ratio in an inert solvent at about -80° C., for approximately 20 minutes; illustrative of such inert solvents are methylene chloride, ether and the like. After a standard workup the product residue is dissolved in an ethereal solvent, chilled to about 0° C. and oxidized with an agent such as 30% hydrogen peroxide or a peroxy acid such as peroxybenzoic acid to yield a halohydrin analog (3). After a standard workup the product residue is dissolved in an ethereal solvent

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

Procedure: To a solution of 2.2 g. (20 mmol) thiophenol in 30 ml. dry ether one adds 1.8 g. pyridine and adds dropwise thereto, with cooling, a solution of 3.2 g. (20 mmol) benzenesulphinic acid chloride in 20 ml. dry ether. One allows to stir further for 10 min., pours into dil. sulphuric acid, separates off the organic phase, dries and evaporates. There remain 3.2 g. of the title compound (68% of theory) of the m.p. 69°-70° C. (from ligroin). with cooling evaporates

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The diene (2) of step (B) is treated with a halogenating agent such as phenylselenyl chloride or bromide or phenylsulfinyl chloride, preferably phenylselenyl chloride, in an approximately equimolar ratio in an inert solvent at about -80° C., for approximately 20 minutes; illustrative of such inert solvents are methylene chloride, ether and the like. After a standard workup the product residue is dissolved in an ethereal solvent, chilled to about 0° C. and oxidized with an agent such as 30% hydrogen peroxide or a peroxy acid such as peroxybenzoic acid to yield a halohydrin analog (3). After a standard workup the product residue is dissolved in an ethereal solvent

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The diene (2) of step (B) is treated with a halogenating agent such as phenylselenyl chloride or bromide or phenylsulfinyl chloride, preferably phenylselenyl chloride, in an approximately equimolar ratio in an inert solvent at about -80° C., for approximately 20 minutes; illustrative of such inert solvents are methylene chloride, ether and the like. After a standard workup the product residue is dissolved in an ethereal solvent, chilled to about 0° C. and oxidized with an agent such as 30% hydrogen peroxide or a peroxy acid such as peroxybenzoic acid to yield a halohydrin analog (3). After a standard workup the product residue is dissolved in an ethereal solvent

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The diene (2) is treated with a halogenating agent such as phenylselenyl chloride or bromide or phenylsulfinyl chloride, preferably phenylselenyl chloride, in an approximately equimolar ratio in an inert solvent at about -80° C., for approximately 20 minutes; illustrative of such inert solvents are methylene chloride, ether and the like. After a standard workup the product residue is dissolved in an ethereal solvent, chilled to about 0° C. and oxidized with an agent such as 30% hydrogen peroxide or a peroxy acid such as peroxybenzoic acid to yield a halohydrin analog (3). After a standard workup the product residue is dissolved in an ethereal solvent

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

Procedure: A solution of 13-9 (0.27 g, 0.88 mmol) in H2O/dioxane (2:1, 4.4 mL) was cooled to 0° C. and then treated dropwise with 1N NaOH to attained a pH of 10.5. The reaction mixture was then treated with with PhSOCl (0.23 g, 1.3 mmol) in dioxane (750 μL) while maintaining a pH of 10.5 by adding 1N NaOH. After 15 min, the pH was adjusted to 7 with 1N HCl to effect a white precipitate. The precipitate was collected by filtration and triturated with EtOAc and then ether to give 13-10 as a colorless solid. while maintaining a pH of 10.5 The precipitate was collected by filtration triturated with EtOAc

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

Procedure: 20.8 g (0.1 mol) of 5-methyl-1,3-benzodioxole-2-carboxylic acid ethyl ester Example 2b) and 19.2 g (0.125 mol) of phenylsulphinic acid chloride are dissolved in 200 ml of 1,2-dichloroethane and cooled to 5° using an ice-bath. 13.3 g (0.1 mol) of aluminium chloride are introduced in the course of approximately 15 minutes at from 5°-10° while stirring. The mixture is stirred for a further hour in the ice-bath and is then poured out onto ice-water. The resulting emulsion is diluted with 200 ml of dichloroethane and filtered across a layer of a filter aid (for example Hyflo). The filtrate is introduced into a separating funnel and the layers are separated. The organic phase is dried over sodium sulphate, filtered and concentrated to dryness by evaporation. A light brown honey-like product, 5-phenylsulphinyl-6-methyl-1,3-benzodioxole-2-carboxylic acid ethyl ester, is obtained. cooled to 5° is then poured out onto ice-water The filtrate is introduced into a separating funnel the layers are separated The organic phase is dried over sodium sulphate filtered concentrated to dryness by evaporation