57768-35-1

Upstream product

• 882-33-7 diphenyldisulfane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 21849-30-9 2-benzenesulfinyl-1-oxa-spiro[2.5]octane 
• 930-69-8 sodium thiophenolate 
• 139058-74-5 1-(diacetoxymethyl)-1-(phenylsulfenyl)cyclohexane 
• 53282-55-6 (trimethylsiloxymethylidene)cyclohexane 
• 931-59-9 benzenesulfenyl chloride 
• 13307-57-8 α-Hydroxy-cyclohexancarbaldehyd-diphenylthioacetal 
• 13865-50-4 methoxymethyl phenyl sulfide 
• 75456-59-6 1--1-cyclohexanol 

Downstream Products

• 139747-29-8 3-[Hydroxy-(1-phenylsulfanyl-cyclohexyl)-methyl]-dihydro-furan-2-one 
• 104750-47-2 (2RS,3SR)-methyl 3-hydroxy-2-methyl-3-<1-(phenylthio)cyclohexyl>propionate 
• 104750-47-2 (2R,3R)-3-Hydroxy-2-methyl-3-(1-phenylsulfanyl-cyclohexyl)-propionic acid methyl ester 
• 139747-28-7 3-Hydroxy-2-hydroxymethyl-3-(1-phenylsulfanyl-cyclohexyl)-propionic acid ethyl ester 
• 135967-29-2 4-(1''-Ethoxyethoxy)-1-[1'-(phenylsulfanyl)cyclohexyl]butanol 
• 127940-85-6 (2R,3R)-3-Hydroxy-2-methyl-3-(1-phenylsulfanyl-cyclohexyl)-thiopropionic acid S-phenyl ester 
• 104750-38-1 (2RS,3SR)-2,6-dimethylphenyl 3-hydroxy-2-methyl-3-<1-(phenylthio)cyclohexyl>propionate 
• 138649-97-5 (4S)-3-<(2S,3S)-3-hydroxy-2-methyl-1-oxo-3-(1-phenylsulfanylcyclohexyl)propyl>-4-phenylmethyl-1,3-oxazolidin-2-one 
• 127940-83-4 (2RS,3RS)-3-hydroxy-2-methyl-3-<1-(phenylthio)cyclohexyl>propiononitrile 
• 127940-83-4 (2RS,3SR)-3-hydroxy-2-methyl-3-<1-(phenylthio)cyclohexyl>propiononitrile 
• 174784-03-3 Ethyl 3-hydroxy-3-[1'-(phenylsulfanyl)cyclohexyl]propanedithioate 
• 81650-72-8 [1-(Phenylsulfanyl)cyclohexyl]ethene 
• 165748-29-8 2-[1'-(Phenylsulfanyl)cyclohexyl]epoxyethane 
• 253152-05-5 Ethyl 3-hydroxy-3-[1'-(phenylsulfanyl)cyclohexyl]propanoate 

Relevant academic research and scientific papers

Do the electronic effects of sulfur indeed control the π-selectivity of γ-sulfenyl enones? An investigation

The electronic effects of sulfur in γ-sulfenyl enones are not transmitted to the carbonyl carbon through the π bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising

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.

Transformation of Cyclic α-Phenylthio Aldehydes by Stereoselective Aldol Reactions and Phenylthio Migration into Spirocyclic Lactones and Ethers, and E-Allylic Alcohols with 1,4-Related Chiral Centres

syn- and anti-Selective aldol reactions between enolates of propionate esters and three α-phenylthio cycloalkanecarbaldehydes give single diastereoisomers of phenylthio alcohols which rearrange in acid with 5-hydroxy or 5-CO2H participation to give spiroc

Additive Pummerer reactions of vinylic sulphoxides. Synthesis of 2-(phenylsulphenyl) aldehydes and primary alcohols

Reaction in acetic anhydride solution of α,β-unsaturated sulphoxides 1 with sodium acetate and triflic anhydride gives 2-(phenylsulphenyl) acylals 4. Basic methanolysis of 4 gives 2-(phenylsulphenyl) aldehydes 8, whilst reduction gives directly 2-(phenylsulphenyl) primary alcohols 9.

A novel synthesis of α-(phenylthio)aldehydes

Addition of methoxy(phenylthio)methyllithium to ketones, followed by rearrangement of the adducts, provides a new method for the preparation of α-(phenylthio)aldehydes.The rearrangement is stereospecific.

PHENYLTHIO(PhS) MIGRATION IN THE STEREOCONTROLLED SYNTHESIS OF ALLYLIC ALCOHOLS WITH 1,4 RELATED CHIRAL CENTRES.

Stereoselective aldol products are transformed by PhS migration into lactones, tetrahydrofurans, and, by subsequent Evans-Mislow rearrangement, into the title compounds with complete stereochemical control.

α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. II. A Novel Synthesis of α-Sulfenylated Ketones and α-Sulfenylated Aldehydes from α,β-Epoxy Sulfoxides

Treatment of α,β-epoxy sulfoxides, prepared from 1-chloroalkyl phenyl sulfoxides and carbonyl compounds, with various kinds of alkane- or arenethiolates afforded α-sulfenylated ketones in good yields.This method also offered a novel procedure for a synthe

A NOVEL SYNTHESIS OF α-SULFENYLATED ALDEHYDES

Ketones are converted into α-sulfenylated aldehydes with addition of one carbon atom via reaction with methoxyphenylthiomethyllithium followed by rearrangement of the adducts.