Benzyltriphenylphosphonium Peroxymonosulfate Research Articles

Benzyltriphenylphosphonium Peroxymonosulfate

Benzyltriphenylphosphonium peroxymonosulfate ­(1, ­BTPPMS) is a mild, efficient, stable, and cheap reagent which displays its versatility in organic synthesis. It is a white solid and generally stored at room temperature. It is quite soluble in dichloromethane, chloroform, acetone, and acetonitrile but insoluble in non-polar solvents, such as carbon tetrachloride, n-hexane, and diethyl ether. It has been used for the oxidation of alcohols to aldehydes and ketones under aprotic solvent condition, [¹] oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers under non-aqueous conditions, [²] and selective oxidation of sulfides and thiols to the corresponding sulfoxides and disulfides under solvent-free conditions. [³] It was also found to be useful for the dethioacetalization of 1,3-dithio­lanes and 1,3-dithianes to the corresponding carbonyl compounds in the presence of bismuth chloride under aprotic conditions [4] and conversion of oximes and semicarbazones to carbonyl compounds using microwave irradiation to afford the carbonyl compounds. [5] Because of the mild conditions as well as the high yields, this reagent has wide acceptance in the area of synthetic chemistry.

Metal-free oxidative dehydrogenation of imidazolines and pyrazolines using silica-adsorbed peroxymonosulfate under aprotic and almost neutral conditions

Oxidative dehydrogenation of 1,3,5-trisubstituted pyrazolines and 2-substituted imidazolines to their corresponding pyrazoles and imidazoles is carried out effectively by treatment with benzyltriphenylphosphonium peroxymonosulfate as an oxidant silica-adsorbed under aprotic and almost neutral conditions.

A Convenient and Regioselective Oxidative Bromination of Electron‐Rich Aromatic Rings Using Potassium Bromide and Benzyltriphenylphosphonium Peroxymonosulfate under Nearly Neutral Reaction Conditions.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

A convenient and regioselective oxidative bromination of electron-rich aromatic rings using potassium bromide and benzyltriphenylphosphonium peroxymonosulfate under nearly neutral reaction conditions

Regioselective oxidative bromination of electron-rich aromatic rings has been studied using potassium bromide as a bromine source in the presence of benzyltriphenylphosphonium peroxymonosulfate as oxidant under nearly neutral reaction conditions. In most cases we obtained monobrominated derivatives regioselectively and in good to high yields without the aid of strong acids.

A convenient and efficient protocol for oxidative aromatization of Hantzsch 1,4-dihydropyridines using benzyltriphenylphosphonium peroxymonosulfate under almost neutral reaction conditions

Oxidative aromatization of 4-alkyl or aryl and heterocyclic-substituted derivatives of Hantzsch 1,4-dihydropyridines to the corresponding pyridine derivatives has been studied using benzyltriphenylphosphonium peroxymonosulfate as an oxidant in the presence of BiCl 3 under nearly neutral reaction conditions at ambient temperature.

Highly Selective Iodination of Phenols Using Potassium Iodide and Benzyltriphenylphosphonium Peroxymonosulfate.

ChemInformVolume 35, Issue 41 Isocyclic Compounds Highly Selective Iodination of Phenols Using Potassium Iodide and Benzyltriphenylphosphonium Peroxymonosulfate. Abdol Reza Hajipour, Abdol Reza Hajipour Pharm. Res. Lab., Coll. Chem., Isfahan Univ. Technol., Isfahan 84156, IranSearch for more papers by this authorHadi Adibi, Hadi Adibi Pharm. Res. Lab., Coll. Chem., Isfahan Univ. Technol., Isfahan 84156, IranSearch for more papers by this author Abdol Reza Hajipour, Abdol Reza Hajipour Pharm. Res. Lab., Coll. Chem., Isfahan Univ. Technol., Isfahan 84156, IranSearch for more papers by this authorHadi Adibi, Hadi Adibi Pharm. Res. Lab., Coll. Chem., Isfahan Univ. Technol., Isfahan 84156, IranSearch for more papers by this author First published: 24 September 2004 https://doi.org/10.1002/chin.200441088Citations: 1Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article.Citing Literature Volume35, Issue41October 12, 2004 RelatedInformation

Highly selective iodination of phenols using potassium iodide and benzyltriphenylphosphonium peroxymonosulfate

An easy and selective method for monoiodination of phenols using potassium iodide in the presence of benzyltriphenylphosphonium peroxymonosulfate is presented. The reactions have been carried out in acetonitrile to afford the corresponding iodophenols in moderate to high yields.

Selective and Efficient Oxidation of Sulfides and Thiols with Benzyltriphenylphosphonium Peroxymonosulfate in Aprotic Solvent.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Microwave Assisted Conversion of Oximes and Semicarbazones to Carbonyl Compounds Using Benzyltriphenylphosphonium Peroxymonosulfate.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Microwave Assisted Conversion of Oximes and Semicarbazones to Carbonyl Compounds Using Benzyltriphenylphosphonium Peroxymonosulfate

Benzyltriphenylphosphonium peroxymonosulfate in the presence of catalytic amounts of bismuth chloride was found to be an efficient and mild reagent for the oxidative cleavage of oximes and semicarbazones to the corresponding carbonyl compounds under microwave irradiation.

A Convenient Method for Dethioacetalization of 1,3-Dithiolanes and 1,3-Dithianes Using Benzyltriphenylphosphonium Peroxymonosulfate in Aprotic Solvent

Benzyltriphenylphosphonium peroxymonosulfate in the presence of bismuth chloride was found to be an efficient and mild reagent for the dethioacetalization of 1,3-dithiolanes and 1,3-dithianes to the corresponding carbonyl compounds under aprotic conditions.

Selective and efficient oxidation of sulfides and thiols with benzyltriphenylphosphonium peroxymonosulfate in aprotic solvent.

Benzyltriphenylphosphonium peroxymonosulfate could be used for selective oxidation of aromatic and aliphatic sulfides and thiols to their corresponding sulfoxides and disulfides under nonaqueous and aprotic conditions without catalyst.

A Selective Solid State Oxidation of Sulfides and Thiols with Benzyltriphenylphosphonium Peroxymonosulfate

Benzyltriphenylphosphonium peroxymonosulfate 1 could be used for oxidation of sulfides 2 and thiols 4 to their corresponding sulfoxides 3 and disulfides 5 under solid-phase conditions.

Solid State Deprotection of Acetals and Thioacetals Using Benzyltriphenylphosphonium Peroxymonosulfate

A variety of acetals and thioacetals 2 are deprotected to the corresponding parent carbonyl compounds 3 under solvent-free conditions using benzyltriphenyl-phosphonium peroxymonosulfate (1) in the presence of aluminum chloride.

ChemInform Abstract: Conversion of Oximes, Phenylhydrazones, 2,4‐Dinitrophenylhydrazones, and Semicarbazones to Corresponding Carbonyl Compounds with Benzyltriphenylphosphonium Peroxymonosulfate (BnPh3P+HSO5‐) (BTPPMS) in the Presence of Bismuth Chloride under Non‐aqueous Conditions.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Oxidative Deprotection of Trimethylsilyl Ethers, Tetrahydropyranyl Ethers, and Ethylene Acetals with Benzyltriphenylphosphonium Peroxymonosulfate under Microwave Irradiation.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Oxidation of Urazoles to Triazolinediones with Benzyltriphenylphosphonium Peroxymonosulfate under Solvent‐Free Conditions.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Oxidation of Urazoles to Triazolinediones with Benzyltriphenylphosphonium Peroxymonosulfate under Solvent-Free Conditions

Abstract Benzyltriphenylphosphonium peroxymonosulfate (PhCH2Ph3PHSO5) in the presence of AlCl3 was used as an effective oxidizing reagent for the oxidation of urazoles to their corresponding triazolinediones in high yields under solvent-free conditions.

OXIDATIVE DEPROTECTION OF TRIMETHYLSILYL ETHERS, TETRAHYDROPYRANYL ETHERS, AND ETHYLENE ACETALS WITH BENZYLTRIPHENYLPHOSPHONIUM PEROXYMONOSULFATE UNDER MICROWAVE IRRADIATION

This paper describes the oxidation deprotection of trimethylsilyl ethers, tetrahydrophyranyl ethers and deprotection of ethylene acetals to afford carbonyl compounds using benzyltriphenylphosphonium peroxymonosulfate (1) (PhCH2PPh3HSO5) in the presence of a catalytic amount of bismuth chloride under microwave irradiation. This reagent is a stable white powder, which has been prepared by the dropwise addition of an aqueous solution of benzyltriphenylphosphonium chloride to an aqueous solution of oxone® at room temperature.

CONVERSION OF OXIMES, PHENYLHYDRAZONES, 2,4-DINITROPHENYLHYDRAZONES, AND SEMICARBAZONES TO CORRESPONDING CARBONYL COMPOUNDS WITH BENZYLTRIPHENYLPHOSPHONIUM PEROXYMONOSULFATE (BnPh3P+HSO5 −) (BTPPMS) IN THE PRESENCE OF BISMUTH CHLORIDE UNDER NON-AQUEOUS CONDITIONS

Benzyltriphenylphosphonium peroxymonosulfate (BTPPMS) (1) has been found to be an efficient and novel reagent for the conversion of oximes, phenylhydrazones, 2,4-dinitrophenylhydrazones and semicarbazones to the corresponding carbonyl compounds. The reaction has been performed in acetonitrile under reflux conditions in the presence of a catalytic amount of bismuth chloride.