18245-73-3

Upstream product

• 108-98-5 thiophenol 
• 141-75-3 butyryl chloride 
• 106-31-0 butanoic acid anhydride 
• 107-92-6 butyric acid 
• 623-42-7 butanoic acid methyl ester 
• 5856-82-6 butyryl bromide 
• 882-33-7 diphenyldisulfane 
• 41115-60-0 1-(1H-benzo[d][1,2,3]triazol-1-yl)butan-1-one 
• 100-68-5 methyl-phenyl-thioether 
• 79597-48-1 1-cyclohexenylmethyl phenyl sulfide 
• 56819-74-0 methyl phenyl sulfide α-carbanion 
• 26065-78-1 S-phenyl cyclopropanecarbothioate 
• 100693-33-2 1-cyclohexene 

Downstream Products

• 1129-50-6 N-phenylbutyramide 
• 131436-08-3 r-4-cyclohexyl-c-3,4-dimethyloxetan-2-one 
• 131436-10-7 3-ethyl-4-methyl-4-(4-methylpent-3-enyl)oxetan-2-one 
• 7570-96-9 2-naphthyl phenyl sulfide 
• 71-36-3 butan-1-ol 
• 88649-73-4 (1-Dichloromethylene-butylsulfanyl)-benzene 
• 121651-90-9 S-Phenyl (2R,3S)-2-ethyl-3-N-(R)-α-methylbenzylamino-5-trimethylsilyl-4-pentynethioate 

Relevant academic research and scientific papers

Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters

We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.

Fungicidal Activity of S-Esters of Thiocarboxylic Acids as Antimicrobial Additives to Petroleum Products

Abstract: A variety of aliphatic and aromatic S-esters of thiocarboxylic acids have been tested for antimicrobial activity. The relationship between the chemical structure of the compounds R1SC(O)R2 and their toxicity for microorganisms has been revealed, and the effect of various functional groups on the antimicrobial properties has been shown. The cooling lubricant IKhP-45E with S-aryl thioacetate additives has been tested. It has been shown that the additives used (0.25–0.5 wt %) inhibit the growth of all the studied microorganisms; however, their activity with respect to fungi is higher. The introduction of S-aryl thioacetates provides the resistance of these oils to microbiological deterioration to retain the physicochemical properties for a long period of time.

Aerobic oxidative esterification and thioesterification of aldehydes using dibromoisocyanuric acid under mild conditions: No metal catalysts required

A practical direct method for the direct preparation of esters and thioesters from aldehydes is described. Esters and thioesters were synthesized by oxidative esterification and thioesterification via in situ generated acyl bromide intermediates, which were used to react with various alcohols and thiols. The esterification and thioesterification were readily performed in the presence of dibromoisocyanuric acid in dichloromethane, without any metal catalysts and under mild conditions. By using this reaction protocol, various esters and thioesters were prepared in high yields. This effective method offers a promising approach for the facile esterification and thioesterification of aldehydes.

Acylation of diselenides and disulfides with N-acylbenzotriazoles promoted by SmI2

The acylation of diselenides or disulfides with N-acylbenzotriazoles mediated by SmI2 has been achieved successfully without the presence of HMPA, and the corresponding selenolesters or thioesters have been prepared in good yields.

S-Acylation of aliphatic and aromatic thiols with carboxylic acids and their esters over solid acid catalysts in the gas phase at temperatures above 200 °c

Benzenethiol is reacted with acetic acid in a hydrogen stream over [(Mo6Cl8)Cl4(H2O) 2]·6H2O. Catalytic activity of the clusters appears above 200 °C, yielding S-phenyl thioacetate. The selectivity is 98% at 300 °C. Niobium, tantalum, and tungsten halide clusters with the same octahedral metal framework also catalyze the reaction. Benzoic acid and aliphatic carboxylic acids afford the corresponding S-phenyl carbothioates by reaction with benzenethiol. Aliphatic thiols are also S-acylated to yield the corresponding S-alkyl carbothioates. When carboxylic esters are applied to the reaction with benzenethiol over [(Nb6Cl12)Cl 2(H2O)4]·4H2O at 450 °C, the sterically unhindered moiety of the ester is incorporated into the products: S-phenyl thioacetate or methyl phenyl sulfide is obtained selectively. A Br?nsted acid site developed on the cluster complex by thermal activation is the active site of the catalyst. Hence, solid acids such as silica-alumina, zeolites, and heteropoly acids that are stable above 200 °C also catalyze these reactions.

Rapid and convenient thioester synthesis under phase-transfer catalysis conditions

Various thioesters were obtained through an efficient phase-transfer catalysis method, by treating several thiophenols with different acyl chlorides, in a biphasic system composed of 10% aqueous NaOH and dichloromethane in the presence of tetrabutylammonium chloride. The thiolation reaction was complete in only 5 minutes, at 0C. Taylor & Francis Group, LLC.

Cleavage of S-S bond by Sm/cat. CoCl2 or Sm/cat. CoCl2 · 6H2O system. A novel method for the synthesis of thiolesters

The Sm/cat. CoCl2 or Sm/cat. CoCl2 · 6H2O system promoted dlsulfides to react with anhydrides or acyl chlorides to afford thiolesters in good yields under mild and neutral conditions.

Samarium(II) iodide promoted reductive ring opening reaction of cyclopropane-1,1-dicarboxylic esters. Synthesis of substituted 5-Pentanolides from carbonyl compounds and dimethyl cyclopropane-1,1-dicarboxylate

Dimethyl cyclopropane-1,1-dicarboxylate is readily subjected to reductive ring opening reaction with samarium(II) iodide in the presence of tris(dibenzoyl-methiodo)iron(III). The generated organosamarium intermediate is trapped by aliphatic ketones to aff

A Practical and Efficient Method for the Synthesis of β-Lactones

This paper describes a convenient one-step preparation of β-lactames based on the addition of thiol ester enolates to carbonyl compounds.Under the proper conditions the resulting aldolates undergo spontaneous cyclization to produce β-lactones in good to excellent yield.The new β-lactone synthesis provides access to 2-oxetanones with a variety of substituents and substitution patterns.In general, thiol ester enolates combine with carbonyl compounds to form the less sterically crowded β-lactone diasteromers, and in some cases the reaction proceeds with excellent stereoselectivity.In conjunction with the stereospecific decarboxylation of β-lactones, this chemistry also provides a very attractive approach to the synthesis of substituted alkenes.

Acid-Catalyzed Regioselective Acylation of α-Silylallylic Sulfides and Its Application to a Novel Cyclopentannelation and Furan Annelation

Introduction of a silyl group at the α-position of allylic sulfides, followed by the aluminum chloride-catalyzed reaction of the resulting α-silylallylic sulfides with acid chlorides resulted in regioselective acylation at the γ-position of the allylic system to give γ-acylated vinylic sulfides, chemically equivalent to 1,4-dicarbonyl compounds.Heating of the products in refluxing benzene with an equimolar amount of p-toluenesulfonic acid produced 2-cyclopentanone derivatives.Treatment of the acylated products with an equimolar amount of concentrated sulfuric acid gave α-phenylthiofuran derivatives.These procedures provide a novel method for cyclopentannelation and furan annelation.Keywords - α-silylallylic sulfide; acid chloride; aluminum chloride; acid-catalyzed acylation; vinylic sulfide; 2-cyclopentanone; α-phenylthiofuran; furan; cyclopentannelation; furan annelation