117917-72-3

Upstream product

• 20451-53-0 Phenyl vinyl sulfoxide 
• 594-19-4 tert.-butyl lithium 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 108-98-5 thiophenol 
• 31238-57-0 diphenyl(phenylthiomethyl)phosphine oxide 
• 163977-73-9 3,3-Dimethylbut-1-en-1-yl phenyl sulfide 
• 111698-34-1 (+/-)_S-isopropyl phenylsulfinate 
• 630-19-3 pivalaldehyde 
• 756-79-6 dimethyl methane phosphonate 
• 61382-44-3 (E)-(3,3-dimethylbut-1-en-1-yl)diisobutylaluminum 
• 98-09-9 benzenesulfonyl chloride 
• 124666-23-5 diphenyl((phenylsulfinyl)methyl)phosphine oxide 

Downstream Products

• 132531-79-4 3,3-dimethyl-1-(phenylsulfenyl)-1,2-bis(trifluoroacetoxy)butane 

Relevant academic research and scientific papers

Reinheckel protocol revisited: Synthesis of (E)-α,β-unsaturated sulfoxides

A new synthetic approach to aryl and alkyl α,β-unsaturated sulfoxides is reported. The reaction has been optimized with respect to solvent, temperature, and ratio of reagents. The described procedure allows the synthesis of the title compounds in good yie

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.

Stereoselective synthesis of (E)-Vinyl Sulfoxides by the Horner-Wittig reaction

The Horner-Wittig reaction of sulfinylmethyl-substituted di-phenylphosphane oxides 1-3 with aldehydes is reported. In a straightforward synthesis, (E)-vinyl sulfoxides 4 (R1 = Ph), 5 (R1 = Me) and 6 (R1=pTol) were formed m

CAN- and DDQ-Promoted Oxidation of Alkenyl Sulfides

Vinyl sulfides 1 react with CAN in acetonitrile at room temperature to give radical cations 2A in equilibrium with the thiiranyl radical cations 2B.The reaction products arise from nucleophilic attack of the nitrate counterion at either the sulfur atom of 2A or the trivalent carbon of 2B.The last reaction can proceed through 1,2-shift or displacement of the sulfide moiety.When α-methylenic protons are present in 2B, deprotonation occurs, leading to allyl radicals and, ultimately, to isomeric allyl alcohols.Reactions of 1 with DDQ in acetonitrile afford charge-transfer complexes and then zwitterionic electron-transfer (ET) complexes which can evolve rapidly through intramolecular proton transfer when trans methylenic protons are present.The resulting sulfur-oxygen ?-complexes are responcible for the reaction products mainly through either γ-elimination of DDQH2 or nucleophilic attack at the δ-vinilic carbon followed by displacement of DDQH(1-).

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.