77134-91-9

Upstream product

• 4837-31-4 4-Phenylsulfanyl-morpholine 
• 75-05-8 acetonitrile 
• 110-83-8 cyclohexene 
• 64168-52-1 4'-nitrobenzenesulfenanilide 
• 115-11-7 isobutene 
• 100-42-5 styrene 
• 63235-31-4 benzenesulfenic acid p-anisidide 
• 14933-91-6 N-phenyl-benzenesulphenamide 
• 931-59-9 benzenesulfenyl chloride 
• 882-33-7 diphenyldisulfane 

Relevant academic research and scientific papers

NaI-Mediated Acetamidosulphenylation of Alkenes with Nitriles as the Nucleophiles: A Direct Access to Acetamidosulfides

An example of a transition-metal-free, direct, and efficient acetamidosulphenylation reaction of alkenes using nitriles as the nucleophiles via a radical process is presented. This reaction shows a broad substrate scope and high regioselectivity and provides straightforward access to acetamidosulfide derivatives in moderate to high yields.

Boron Trifluoride-Promoted Reaction of Benzenesulphenanilides with Alkenes in Acetonitrile and Benzonitrile: Amidino- and Amido-sulphenylation of Alkenes

Benzenesulphenanilides (1) react at room temperature with alkenes in acetonitrile or benzonitrile in the presence of boron trifluoride-diethyl ether to give amidino sulphides (5; R=Me, Ph) in fair to good yields together with varying amounts of amido sulphides (7; R=Me, Ph) and arylamino sulphides (4), whereas at 100 deg C and in the presence of water 4'-nitrobenzenesulphenanilide affords amido sulphides (7; R=Me, Ph) as the main products.With cyclohexene a high selectivity for trans-addition is observed.With terminal alkenes the terminal sulphides are produced with high regioselectivity.The findings are consistent with a mechanism involving intermediacy of episulphonium ions (3) which result from alkene attack at the sulphur atom of an anilide-BF3 complex.

THERMAL REACTIVITY OF 4'SUBSTITUTED- AND 4'-SUBSTITUTED-2-PHENYL-BENZENESUPHENANILIDES

The thermal decomposition of 4'-nitro, 4'-H, and 4'-methoxy-benzenesulphenanilides in benzene and/or furan, and of 4'-substituted-2-phenylbenzenesulphenanilides ( 1d-1f ) in benzene, was found to proceed by two distinct pathways: ( i ) nucleophilic displacement by furan and/or another sulphenanilide unit and ( ii ) homolytic S-N bond fission to give sulphenyl and anilino radicals.An increase in the electron-withdrawning capability of the 4'-substituted favours the ionic pathway, whwreas the radical pathway is favoured by an increase in the reaction temperature.

Anodic Acetamidosulphenylation of Alkenes via Anodic Oxidation of Disulphides

Anodic oxidation, at platinum and carbon electrodes, of dimethyl, diphenyl, dibenzyl, and heterocyclic disulphides in acetonitrile in the presence of alkenes affords products of acetamidosulphenylation.With cyclic alkenes a high selectivity for trans-addi

Additions to Alkenes via Metal Ion-Promoted Oxidation of Dialkyl and Diaryl Disulphides

Reactions of alkenes with di-n-propyl, diphenyl, and dibenzyl disulphide in the presence of lead(IV) salts in trifluoroacetic acid-dichloromethane are described.The products, vicinal trifluoroacetoxysulphides, are obtained in higher yields with manganese(III) salts as the oxidant.Alternative reaction conditions with use of iron(III) salts or in the absence of added metal salts are also described.Trifluoroacetoxysulphides derived from diphenyl disulphide react with acetonitrile under Ritter conditions to give acetamidosulphides but trifluoroacetoxysulphides derived from dibenzyl disulphide only give the vicinal acetamidosulphides in poor yield as a result of an alternative reaction pathway affording benzylacetamide.Conversions of acetamidosulphides into aminosulphides and into acetamidothiols are described.

AMIDINOSULPHENYLATION OF ALKENES

Phenylsulphenamides react chemoselectively with an alkene and a nitrile in the presence of trifluoromethanesulphonic acid to give N-(β-phenylthioalkyl)amidines; in the absence of nitrile an amine is formed.

SYNTHESIS OF ACETYLAMINO SULFIDES BY ELECTROPHILIC ADDITION TO ALKENES

A preparative method is proposed for the production of acetylamino sulfides on the basis of the previously developed method of increasing the effective electrophilicity of weak electrophiles in the presence of perchlorates.

Anodic Acetamidosulfenylation of Alkenes

Anodic oxidation of disulfides in acetonitrile in the presence of an alkene gives acetamidosulphides.