90425-30-2

Upstream product

• 94535-33-8 ethyl 2-(phenylthio)propanoate 
• 535-11-5 Ethyl 2-bromopropionate 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 7605-25-6 ethyl phenylsulfenylacetate 
• 535-13-7 2-chloro-propanoic acid, ethyl ester 

Downstream Products

• 66693-06-9 ethyl 2-(benzenesulfonyl)propanate 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 140-88-5 ethyl acrylate 
• 83182-17-6 ethyl α-sulfinylphenylacrylate 
• 56685-62-2 ethyl 2-(phenylsulfanyl)acrylate 

Relevant academic research and scientific papers

Radical mechanism in the elimination of 2-arylsulfinyl esters

The mechanism of the dehydrosulfenylation of 2-arylsulfinyl esters was investigated. The reaction was found to follow a homolytic cleavage mechanism as verified by electrospray ionization tandem mass spectrometry and experimental work. Rearranged sulfoxides are obtained as byproduct during the elimination reaction.

Oxidation of sulfides with N-bromosuccinimide in the presence of hydrated silica gel

An efficient and highly selective procedure for oxidation of sulfides to sulfoxides with N-bromosuccinimide (NBS) in the presence of hydrated silica gel has been developed. Hydrated silica gel supplies the water necessary for decomposition of the intermed

Selective and mild oxidation of sulfides to sulfoxides by oxodiperoxo molybdenum complexes adsorbed onto silica gel

Aliphatic and aromatic sulfides, ketosulfides, sulfinyl acids and esters, and olefinic sulfides were oxidized to sulfoxides using oxodiperoxo complexes of molybdenum coated on silica gel (150 ? pore size) in very high yields. Complete chemoselectivity was observed for the oxidation of all functional sulfides. Sulfones were, however, the main products of the reaction when the complexes were not coated on silica gel. The influence of silica gel as the support of these reactions was also investigated and it was demonstrated that it alters the reactivity of the complex but it is not responsible for the excellent chemoselectivity of the complexes. The complex [MoO(O2)2(pyrazole) (H2O)] proved to be more reactive than [MoO(O2)2(Opyr) (H2O)].

A facile and selective procedure for oxidation of sulfides to sulfoxides with molecular bromine on hydrated silica gel in dichloromethane

A new method for oxidation of sulfides to sulfoxides with molecular bromine on a solid silica gel support has been developed. This procedure cleanly oxidizes sulfides to the corresponding sulfoxides in excellent yields. To our knowledge, this is the first

A simple and efficient procedure for oxidation of sulfides to sulfoxides on hydrated silica gel with ceric ammonium nitrate (CAN) in methylene chloride

A simple, fast and efficient procedure for oxidation of sulfides to the corresponding sulfoxides with CAN mediated by hydrated silica gel in methylene chloride has been developed. To our knowledge, this is the first example of oxidation of sulfides with C

Chemoselective oxidation of sulfides to sulfones with magnesium monoperoxyphthalate (MMPP) on silica gel support in methylene chloride solvent

A simple, efficient and chemoselective, non-aqueous procedure for oxidation of sulfides to the corresponding sulfones with magnesium monoperoxyphthalate on hydrated silica gel has been developed.

A facile and selective procedure for oxidation of sulfides to sulfoxides on silica gel supported magnesium monoperoxyphthalate (MMPP) in dichloromethane

The scope of the magnesium monoperoxyphthalate (MMPP) oxidation of sulfides to sulfoxides has been extended by using hydrated silica gel as a solid support in dichloromethane media. This procedure works in the presence of a number of functional groups on the sulfides, including carbonyl and alkene groups that have been known to undergo Baeyer-Villiger oxidation and epoxidation with MMPP when using more conventional procedures. To our knowledge, this is the first example of oxidation of sulfides containing a carbonyl group with MMPP in non-aqueous media without any Baeyer-Villiger reaction. The reported procedure is easy to perform, product separation is trivial and it produces excellent yields.

α-Fluorination of methyl phenyl sulfoxide and related compounds by molecular fluorine: A novel method for the introduction of fluorine into sulfoxides bearing α-H atoms

Direct formation of α-fluorosulfones from sulfoxides bearing α-H atoms merely by reaction with molecular fluorine (5% F2/N2) is reported, and a novel non-Pummerer-type mechanism is proposed for this α-fluorination reaction.

PYROLYSIS OF α-ACYL SUBSTITUTED ETHYL PHENYL SULFOXIDE

The effect of pyrolysis of the acyl group substituted on α-position carbon in S-ethyl group of ethyl phenyl sulfoxide was investigated by using two kinds of substrates, 1-ethoxycarbonylethyl phenyl sulfoxide (1) and 1-ethoxycarbonyl-1-methylethyl phenyl sulfoxide (2) together with 2-methoxycarbonylethyl phenyl sulfoxide (4).The rate of pyrolysis of (1) was found to be about 740 ca. 890 times faster than that of ethyl phenyl sulfoxide (5), while (2) was 5700 times faster.The rate enhancement effect on α-ethoxycarbonyl group was larger than that on β-methoxycarbonyl group.Large deuterium kinetic isotope effect (kH/kD=5.5 for PhS(O)C(CD3)2CO2Et (3)) was observed.Activation energy for (2) is about 110 kJ/mol, which is just about the same as that of (5) (108 kJ/mol), while activation entropy lies in ca. 1 Jdeg-1 mol-1.Hammett plot for substituted (2) gave ?=0.69.These kinetic results reveal that the pyrolysis of the sulfoxides proceeds via a loose transition state involving advanced C-S bond cleavage.The remarkably large rate enhancement by α-carbonyl group might be due mainly to the conjugation of that group and developing double bond acidifying the β-proton in the transition state.Key words: Pyrolysis; elimination; mechanism; isotope effect; kinetics; sulfoxide,

Synthesis of α-Phenylthio Enones and Esters of α-Phenylthio Alkenoic Acids

The title compounds can be made by a Pummerer dehydration from the corresponding saturated sulphoxides.The alkylation of anions from saturated and unsaturated ketones is described.