13884-92-9

Usage

Chemical Properties

Off-White to Pale Beige Solid

Uses

Different sources of media describe the Uses of 13884-92-9 differently. You can refer to the following data:
1. A Wittig reagent.
2. A Wittig reagent

InChI:InChI=1/C25H22PS.ClH/c1-5-13-22(14-6-1)26(23-15-7-2-8-16-23,24-17-9-3-10-18-24)21-27-25-19-11-4-12-20-25;/h1-20H,21H2;1H/q+1;/p-1

Upstream product

• 7205-91-6 phenylthiomethyl chloride 
• 603-35-0 triphenylphosphine 
• 2373-51-5 chloro-methylsulfanyl-methane 
• 7205-94-9 chloromethyl phenyl sulfoxide 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 34884-33-8 (phenylthio)-methylenetriphenylphosphorane 
• 75-36-5 acetyl chloride 
• 142-61-0 Hexanoyl chloride 
• 874-60-2 4-methyl-benzoyl chloride 
• 98-88-4 benzoyl chloride 

Downstream Products

• 50550-52-2 1-butenyl phenyl sulfide 
• 101910-04-7 (Z)-(3R,5R)-7-(2,4-Dichloro-phenyl)-1-phenylsulfanyl-hept-1-ene-3,5-diol 
• 123518-27-4 (Z)-4,5-di-O-acetyl-1,2-didehydro-1,2,6-trideoxy-3-O-methyl-1-(phenylthio)-L-arabino-hexose 
• 123518-23-0 (E)-4,5-di-O-acetyl-1,2-didehydro-1,2,6-trideoxy-3-O-methyl-1-(phenylthio)-L-arabino-hexose 
• 791-28-6 Triphenylphosphine oxide 
• 34884-33-8 (phenylthio)-methylenetriphenylphosphorane 
• 58431-66-6 E-3-methyl-but-1-en-1-yl phenyl sulphide 
• 58431-65-5 Z-3-methyl-but-1-en-1-yl phenyl sulphide 
• 58431-64-4 1-(1-Phenylthioethyl)-triphenylphosphoniumiodid 
• 32291-84-2 cis-2-(4-chlorophenyl)-2-(phenylthio)ethylene 
• 32291-83-1 1-(4'-chlorophenyl)-2-(phenylsulfanyl)ethene 
• 92163-57-0 (4-nitrostyryl)(phenyl)sulfane 
• 7214-56-4 phenyl(styryl)sulfane 
• 7214-53-1 (E)-[2-(phenylsulfanyl)vinyl]benzene 

Relevant academic research and scientific papers

Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts

Phosphines were previously unusable as Pummerer-type nucleophiles due to competing redox chemistry with sulfoxides. Here we circumvent this problem to achieve a formal phosphine Pummerer reaction that offers thioalkyl phosphonium salts that, in turn, give rise to diverse vinyl sulfides via Wittig olefinations. Thirty vinyl sulfides are thus prepared from (alkylthioalkyl)triphenyl phosphonium salts and aldehydes. The hydrolysis of these vinyl sulfides offers an efficient and versatile two-step one-carbon homologation of aldehydes to ketones.

Highly selective activation of vinyl C-S bonds over aryl C-S bonds in the Pd-catalyzed coupling of (E)-(β-trifluoromethyl)vinyldiphenylsulfonium salts: Preparation of trifluoromethylated alkenes and dienes

We describe the Suzuki coupling reaction of (E)-(β-trifluoromethyl) vinyldiphenylsulfonium salts with arylboronic acid. The highly efficient and selective reaction provides a useful and mild method for the synthesis of trifluoromethylated alkenes and dienes. Subsequent DFT studies showed that the oxidative addition transition state of the vinyl C-S bond is much more favorable (11.7 kcal mol-1) than that of the aryl C-S bond. Copyright

Base-catalysed intramolecular hydroamination of vinyl sulfiies

Small amounts of n-butyllithium catalyse the highly efficient hydroamination of a large variety of vinyl sulfides. This novel methodology offers an easy access to a wide range of nitrogen heterocycles, including simple pyrrolidines and piperidines, as well as more complex bicyclic compounds. Subsequent transformations of the sulfur group led to the formation of functionalised alkaloid-like substructures. Wiley-VCH Verlag GmbH & Co. KGaA.

In vivo anti-chagas vinylthio-, vinylsulfinyl-, and vinylsulfonylbenzofuroxan derivatives

New benzofuroxans were developed and studied as antiproliferative Trypanosoma cruzi agents. Compounds displayed remarkable in vitro activities against different strains, Tulahuen 2, CL Brener and Y. Its unspecific cytotoxicity was evaluated using human macrophages being not toxic at a concentration at least 8 times, and until 250 times, that of its T. cruzi IC50. Some biochemical pathways were studied, namely parasite respiration, cysteinyl active site enzymes and reaction with glutathione, as target for the mechanism of action. Not only T. cruzi respiration but also Cruzipain or trypanothione reductase were not affected, however the most active derivatives, the vinylsulfinyl- and vinylsulfonyl-containing benzofuroxans, react with glutathione in a redox pathway. Furthermore, the compounds showed good in vivo activities when they were studied in an acute murine model of Chagas' disease. The compounds were able to reduce the parasite loads of animals with fully established T. cruzi infections.

A simplified preparation of vinyl sulfides, selenides and tellurides by a Wittig-type reaction

The preparation of several vinyl sulfides, selenides and tellurides by Wittig-type reaction in a one-pot procedure is described. The chalcogenyl triphenylphosphoranes 3 are formed 'in situ' by the reaction of chloromethyl phenyl chalcogenide, potassium tert-butoxide and triphenylphosphine. Reaction of 3 with carbonyl compounds affords the vinyl chalcogenides 6-9 with preferential Z-configuration.

PYROLYSIS OF α-ACYL,α-THIO PHOSPHORANES THIOACETYLENES

Pyrolysis of α-acyl,α-thio phosphoranes affords thioacetylenes in a good yield.The thio acethylenes are precursors of terminal and alkyl disubstituted acetylenes.

Synthesis and Crystal Structure of Triphenylphosphorane

In order to elucidate preferred conformations in chalkogen-substituted phosphorus ylides, the title compound (C6H5)3P=C(SC6H5)SeC6H5 (4) has been prepared from (chloromethyl)phenylsulfide (1) via triphenylphosphorane (3). 4 is trans