35034-34-5

Upstream product

• 1498-99-3 styrenesulfide 
• 96-09-3 styrene oxide 

Downstream Products

• 649884-96-8 bis{(S)-2-hydroxy-2-phenylethyl} disulfide 

Relevant academic research and scientific papers

Equilibrium shift induced by chiral nanoparticle precipitation in rhodium-catalyzed disulfide exchange reaction

Chiral silica (P)-nanoparticles grafted with (P)-helicene recognize the molecular structure of a chiral diol disulfide in the presence of monool disulfide and dibutyl disulfide. The (P)-nanoparticles selectively adsorb the diol disulfide, aggregate, and precipitate from solution. Under rhodium-catalyzed equilibrium among three disulfides, the diol disulfide is removed from solution by precipitation, which induces an equilibrium shift in the solution. By conducting the precipitation experiment twice, we obtained the diol disulfide in 37% yield from a statistical 1:2:1 equilibrium mixture of three disulfides. The method is applied to a racemic monool disulfide, and an optically active diol disulfide is obtained via kinetic resolution and equilibrium shift.

Reactions of epoxides and episulfides with electrophilic halogens

A novel method is described for the conversion of epoxides into β-bromoformates using Ph3PBr2, Ph3P/N-bromosuccinimdes (NBS) and or Ph3P/2,4,4,6-tetrabromo-2,5-cyclohexadiene-1-one (TABCO) in DMF. Epoxides in the presence of Ph3P/I2 were converted into olefins immediately in excellent yields. The application of NBS, NCS, and TABCO as compounds carrying electrophilic halogens for the highly selective alcoholysis of epoxides and dimerization or alcoholysis dimerization of episulfides are also described.

Aminopropyl silica gel supported iodine as catalyst in nucleophilic ring opening of epoxides and episulfides

Silica gel functionalized by aminopropyl group was prepared. Iodine was then supported on this inorganic polymer and used as a stable and efficient heterogeneous catalyst for nucleophilic ring opening reactions of epoxides and episulfides in different nucleophilic solvents such as alcohols, water and acetic acid.

A new stable modified borohydride reagent. Efficient reduction of different functional groups with sulfurated barium borohydride [Ba(BH2S3)2] in dry THF

Barium and strontium sulfurated borohydrides, Ba(BH2S3)2,Sr(BH2S3) 2 the two newly introduced modified borohydride agents, are prepared from NaBH2S3 by metathesis reaction with BaCl2 and SrCl2 in good yields. Ba(BH2S3)2 is more stable and more reactive than Sr(BH2S3)2. The reducing ability of Ba(BH2S3)2 for the reduction of aldehydes, ketones, α,β-unsaturated carbonyl compounds, azides, nitro compounds, and cleavage of epoxides in dry THF is described.

Efficient reduction of organic compounds with sulfurated calcium borohydride [Ca(S3BH2)2], a new and stable modified borohydride reagent

Sulfurated Calcium, magnesium, and berelium horohydrides are prepared by metathetical reaction between NaBH2S3 and Ca, Mg, and Be chlorides in dry THF and the effect of metal cation exchange on their stability and reactivity has been presented. In this study we have shown that Ca(BH2S3)2 is much more stable and more reactive than its Mg, Be, and Na analogues. Ca(BH2S3)2can easily reduce carbonyl compounds such as aldehydes, ketones, acyloins, α-diketones, α-β-unsaturated carbonyl compounds, aroyl azides, and carboxylic acid chlorides to their corresponding alcohols in good to excellent yields. Epoxides are also effected by this reagent and produce their symmetrical dihydroxydisulfides in good yields.

Highly efficient, regio- and stereoselective ring opening of epoxides and thiiranes with Ce(OTf)4

Ceric triflate, Ce(OTf)4 is used as an efficient catalyst for ring opening of epoxides in the presence of alcohols, water, and acetic acid. The reactions proceed with high regio and stereoselectivity and in excellent yields. The reaction of R(+) styrene oxide with methanol occurs with excellent optical purity. Ring opening of thiiranes in alcohols, water and acetic acid followed by dimerisation to the corresponding disulfides occur efficiently in the presence of this reagent. A mild method for the preparation of dithianes from thiiranes and Ce(OTf)4 is also described.

Iodine and iodine supported on polyvinylpyrrolidone as catalysts and reagents for alcoholysis, hydrolysis, and acetolysis of epoxides and thiiranes

Iodine and iodine supported on polyvinylpyrrolidone (betadine) have been used as catalysts for ring opening of epoxides and as reagent for ring-opening dimerization of thiiranes in alcohols, water, and acetic acid. The reactions occur with high regio-, chemo-, and stereoselectivity. The reaction of R-(+)-styrene oxide with I2 supported on PVP in methanol was found to be very stereospecific and the product was isolated in 93% ee.