40110-65-4

Upstream product

• 74031-47-3 (Z)-((2-bromoethenyl)sulfinyl)benzene 
• 23402-69-9 lithium diphenylcuprate 
• 111698-34-1 (+/-)_S-isopropyl phenylsulfinate 
• 100-52-7 benzaldehyde 
• 756-79-6 dimethyl methane phosphonate 
• 7214-56-4 phenyl(styryl)sulfane 
• 16619-61-7 1-phenyl-2-phenylthioethene 
• 7205-91-6 phenylthiomethyl chloride 
• 100-42-5 styrene 
• 4972-29-6 benzenesulphinyl chloride 
• 108-98-5 thiophenol 
• 536-74-3 phenylacetylene 
• 178321-37-4 Phenylsulfanylmethyl-phosphonic acid bis-(2,2,2-trifluoro-ethyl) ester 
• 35460-31-2 (2-phenylsulfanylethynyl)benzene 

Downstream Products

• 80232-39-9 (4R,5S)-3,3-Dichloro-4-phenyl-5-phenylsulfanyl-dihydro-furan-2-one 
• 117917-58-5 (R_C^*R_S^*)-2-(dimethylphenylsilyl)-2-phenylethyl phenyl sulfoxide 
• 117917-58-5 (S_C^*R_S^*)-2-(dimethylphenylsilyl)-2-phenylethyl phenyl sulfoxide 
• 117917-64-3 C₂₂H₂₃⁽²⁾HOSSi 
• 117917-64-3 C₂₂H₂₃⁽²⁾HOSSi 
• 139058-68-7 (+/-)-1,1-diacetoxy-2-phenyl-2-(phenylsulphenyl)ethane 
• 113107-63-4 methyl 4-tert-butyldimethylsiloxy-3-phenyl-4-(phenylthio)butanonate 
• 132531-83-0 2-phenyl-1-(phenylsulfenyl)-1,2-bis(trifluoroacetoxy)ethane 
• 7214-56-4 phenyl(styryl)sulfane 
• 117917-76-7 C₁₆H₁₇⁽²⁾HSi 
• 117917-75-6 C₁₆H₁₇⁽²⁾HSi 
• 882-33-7 diphenyldisulfane 
• 51212-29-4 β-formylbenzenepropanoic acid methyl ester 
• 582-24-1 1-phenyl-2-hydroxyethanone 

Relevant academic research and scientific papers

Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant

Sulfoxides are important functional molecules. We develop a short-route (one-pot) synthesis of this class of molecules by reacting thiols with alkenes or alkynes under mild and metal-free conditions. N-Fluorobenzenesulfonimide (NFSI) is used to play dual roles: as a radical initiator for a thiol-ene/-yne reaction to form sulfide adducts, and as efficient oxidant for conversion of the sulfides formed in situ to sulfoxides. Over-oxidation of the sulfoxides to sulfones is avoided in our approach.

Acid-Catalyzed Oxidative Addition of Thiols to Olefins and Alkynes for a One-Pot Entry to Sulfoxides

An oxidative variant of the thiol-ene reaction has been developed, achieving the direct addition of thiols to olefins to form sulfoxides. The reaction uses tert-butyl hydroperoxide as oxidant and methanesulfonic acid as catalyst. The latter is believed to catalyze the oxidation of the intermediate sulfide to the sulfoxide. No special precautions are necessary to exclude oxygen, yet the products are formed without oxidation at the β-position. Styrenes, acrylic acid derivatives, alkynes, and thiophenols gave the highest yields, while aliphatic olefins and thiols were less effective.

Synthesis of vinyl sulfoxides using sulfinyl chlorides and olefins

A general method for synthesis of vinyl sulfoxides, using sulfinyl chlorides and olefins as starting materials and DBU as an HCl scavenger, has been developed. Vinyl sulfoxides were obtained from the ZnCl2 catalysed addition of sulfinyl chlorides to olefins followed by the elimination with DBU. However, the direct reaction of sulfinyl chlorides with olefins in the presence of DBU, usually leads to generation of vinyl sulfones. The sulfonyl radicals generated from the DBU-mediated disproportionation of the sulfinyl radicals undergo addition-elimination reaction with olefins to give vinyl sulfones.

Stereo-recognizing transformation of (E)-alkenyl halides into sulfides catalyzed by nickel(0) triethyl phosphite complex

(E)-Alkenyl halides were transformed into (E)-alkenyl sulfides by the nickel(0) triethyl phosphite complex-catalyzed reaction with thiols, whereas (Z)-alkenyl halides gave alkynes under the same reaction conditions. Aryl halides were also transformed into aryl sulfides using the same reagent system.

A selective and convenient oxidation of acetylenic sulfides to acetylenic sulfoxides using trichloroisocyanuric acid

Acetylenic sulfides are readily oxidized to acetylenic sulfoxides by a solution of pyridine, water, benzoic acid and trichloroisocyanuric acid in acetonitrile and methylene chloride.

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)].

Hydrozirconation of alkynyl sulfoxides: The reactions of zirconated vinyl sulfoxide intermediates

Alkynyl sulfoxides react with Cp2Zr(H)Cl in THF at room temperature to give the α-zirconated and β-zirconated vinyl sulfoxides, which react with a wide range of electrophiles to give several types of di- or trisubstituted olefins, such as Z-vinyl sulfoxides and α- or β-halo vinyl sulfoxides. (C) 2000 Elsevier Science Ltd.

Stereoselective synthesis of racemic and optically active E-vinyl and E- dienyl sulfoxides via Wittig reaction of α-sulfinyl phosphonium ylides

A series of α-sulfinyl phosphonium ylides have been obtained in the reaction of phosphonium mono- and diylides with sulfinic acid esters. The use of (-)-(S)-menthyl p-toluenesulfinate in this reaction afforded the corresponding (S)-((p-tolylsulfinyl)methyl)triphenylphosphonium ylide. The Wittig reaction of these ylides with saturated and unsaturated aldehydes resulted in the formation of racemic and optically active (+)-(R)-vinyl and dienyl sulfoxides with the E-geometry. The synthesis of (+)-(R)-((p- tolylsulfinyl)methyl)triphenylphosphonium iodide as a precursor of the optically active ylide has also been described.

Selective synthesis of cis-α,β-unsaturated sulfoxides and sulfides by the Horner-Wittig reaction with bis(2,2,2-trifluoroethyl)phosphono sulfoxides and aromatic aldehydes

cis-α,β-Unsaturated sulfoxides were predominantly formed in the Horner-Wittig reaction with bis(2,2,2-trifluoroethyl)phosphono sulfoxides and aromatic aldehydes, while the reaction of the corresponding sulfides showed trans- or lower cis-selectivity. The reduction of cis-α,β-unsaturated sulfoxides with tributylphosphine in carbon tetrachloride gave cis-vinyl sulfides with retention of stereochemistry.

Additive Pummerer reactions of vinylic sulfoxides. Synthesis of γ-hydroxy-α,β-unsaturated esters, α-hydroxyketones, and 2-phenylsulfenyl aldehydes and primary alcohols

Treatment of β-monosubstituted vinylic sulfoxides 1 with trifluoroacetic anhydride in dichloromethane gave excellent yields of 1,2-bis(trifluoroacetoxy)thioethers 6. Mildly basic methanolysis of 2-alkyl-substituted 6 gave α-hydroxyaldehydes 11 as monomer-dimer mixtures; similar treatment of the 2-aryl analogues afforded aryl (hydroxymethyl) ketones 12. Compounds 11 underwent Wittig reactions with methoxycarbonylmethylenetriphenylphosphorane to give high yields of γ-hydroxy-α,β-unsaturated esters 13, predominantly as the E-isomers. β-Monosubstituted vinylic sulfoxides 1 possessing a β-aryl group, and β-disubstituted vinylic sulfoxides 3 reacted with trifluoromethanesulfonic anhydride-sodium acetate in acetic anhydride to give 2-(phenylsulfenyl) acylals 14. These gave 2-phenylsulfenyl aldehydes 15 upon basic methanolysis, and the corresponding primary alcohols 16 on reduction with sodium borohydride. Reaction of both geometric isomers of enantiomerically pure vinylic sulfoxide 1o with TFAA gave racemic 6o as a mixture of diastereomers. Reaction of optically pure (E)- and (Z)-1p with trifluoromethanesulfonic anhydride-sodium acetate in acetic anhydride gave acylal 19 in 10.5 and 23% e.e., respectively.