70004-05-6

Upstream product

• 111-71-7 heptanal 
• 111698-34-1 (+/-)_S-isopropyl phenylsulfinate 
• 756-79-6 dimethyl methane phosphonate 
• 629-05-0 n-octyne 
• 108-98-5 thiophenol 
• 42599-17-7 (E)-1-iodo-1-octene 
• 40098-43-9 diisobutyl[(1E)-oct-1-en-1-yl]aluminum 
• 98-09-9 benzenesulfonyl chloride 
• 69036-39-1 1-octen-1-yl phenyl sulfide 

Downstream Products

• 132531-75-0 1-(phenylsulfenyl)-1,2-bis(trifluoroacetoxy)octane 
• 77727-25-4 C₁₇H₂₆O₃S 
• 77727-25-4 C₁₇H₂₆O₃S 
• 59614-86-7 (3S)-3-Methylnonanoic acid 
• 98750-72-2 (1,2-Dichloro-octylsulfanyl)-benzene 
• 77727-23-2 (E)-2-((S)-Benzenesulfinyl)-non-2-enoic acid methyl ester 

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.

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.

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

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.