74455-32-6

Upstream product

• 4837-31-4 4-Phenylsulfanyl-morpholine 
• 1745-81-9 o-Allylphenol 
• 882-33-7 diphenyldisulfane 
• 931-59-9 benzenesulfenyl chloride 
• 873-55-2 sodium benzenesulfonate 
• 4972-31-0 1-benzenesulfinyl piperidine 

Downstream Products

• 101041-35-4 2-Benzenesulfonylmethyl-2,3-dihydro-benzofuran 
• 126708-25-6 5-Chloro-2-(dichloro-phenylsulfanyl-methyl)-2,3-dihydro-benzofuran 

Relevant academic research and scientific papers

Copper-Catalyzed Oxysulfenylation of Enolates with Sodium Sulfinates: A Strategy to Construct Sulfenylated Cyclic Ethers

A new copper-catalyzed oxysulfenylation reaction of enolates with sodium sulfinates has been disclosed. A series of sulfenylated heterocycles including four- and seven-membered cyclic ether were obtained in mild to good yields. This reaction is proposed to go through a radical process, and the sulfur radical (RS?) may be a reactive species.

Cyclofunctionalization of unsaturated alcohols, phenols, acids, and sulfonamides with 1-benzene-sulfinyl piperidine and trifluoromethanesulfonic anhydride

The combination of a benzenesulfinamide, trifluoromethanesulfonic anhydride, and Huenig's base brings about the cyclofunctionalization of unsaturated alcohols, phenols, acids, and sulfonamides to give the corresponding α-phenylsulfanylmethyl cyclic ethers, lactones and sulfonamides, respectively. In an unanticipated twist the products are isolated at the sulfur (II) oxidation state denoting an overall reduction in the oxidation state of the sulfur based electrophile in the course of the reaction.

Synthesis of methyl 2,3-dihydro-2-benzofurancarboxylates from o-allylphenols via 2-(phenylthiomethyl)-2,3-dihydrobenzofurans

A method for synthesizing methyl 2,3-dihydro-2-benzofurancarboxylates rom o-allylphenols is described.The reaction of 6allyl-2,3-dichlorophenol (3) with benzenesulfenyl chloride (PhSCl) in acetonitrile gave a mixture of PhSCl -adducts, which was heated in aqueous acetonitrile then with sodium bicarbonate to obtain 6,7-dichloro-2-(phenylmethyl)-2,3-dihydrobenzofuran (6). α-Dichlorination of the phenylthiomethyl group of 6 and subsequent methanolysis gave the methyl ester 5 in high yield.The generality of this synthetic method was examined by the conversion of o-allylphenols 11 having various substituents on the benzene ring into the corresponding methyl ester 23.Cyclization of 11 to sulfides 12 could be achived similerly to the case of 3.However, in the subsequent conversions of 12 to 23, selective α-dichlorination followed by methanolysis could be achived only with 12 substituted with an electron-withdrawing group such as a chloro or nitro group.Keywords - oallylphenils; methyl 2,3-dihydro-2-benzofurancarboxylate; 2-(phenylthiomethyl)-2,3-dihydrobenzofuran; benzenesulfenyl chloride; α-chlorination; methanolysis.

INTRAMOLECULAR ARYLSULPHOETHERIFICATION AND LACTONIZATION OF UNSATURATED ALCOHOLS AND CARBOXYLIC ACIDS INITIATED BY ANODIC OXIDATION OF DISULPHIDES

The intramolecular sulphoetherification respectively sulpholactonization of alkenols and alkenoic acids can be initiated by addition of electrochemically generated sulphenyl cations starting from disulphides.The reaction can either be initiated by indirect electrochemical oxidation of diphenyldisulphide using bromide as redox catalyst or preferably by direct anodic oxidation of bis(4-methoxyphenyl)disulphide. 5- and 6-membered thioaryl substituted ethers and lactones thus may be generated starting preferably from mono or disubstituted alkenols and alkenoic acids.The reaction occurs as a trans-addition to the double bond while for endocyclic double bonds the new ring is cis-annelated.

Cyclic Ether Formation with N-(Phenylthio)morpholine

Cyclic ethers with 5- to 7-membered rings are formed by sulphenoetherification of unsaturated alcohols with N-(phenylthio)morpholine and trifluoromethanesulphonic acid.

Cyclofunctionalization of 2-Allyl-phenols with Sulfur Chlorides. Synthesis of 2,3-Dihydrobenzofurfuryl Thioethers by the Reaction of 2-Allyl-phenols with Aromatic Sulfenyl Chlorides

Reactions of different substituted 2-allyl-phenols (2a-h) with either phenylsulfenyl chloride (3) or 4-methyl phenylsulfenyl chloride (4) yield the products of a cyclofunctionalization 2-phenylthiomethyl 2,3-dihydrobenzofuranes (6a-h) or 2-(4'-methylpheny