97852-39-6

Upstream product

• 542-75-6 E/Z-1,3-Dichloropropene 
• 104-88-1 4-chlorobenzaldehyde 
• 113662-35-4 (Z-3-chloroprop-2-enyl)tri-n-butyl stannane 
• 106-95-6 allyl bromide 
• 873-76-7 para-Chlorobenzyl alcohol 
• 89110-81-6 diisobutyl telluronium allylide 
• 132356-17-3 allyldiisobutyltelluronium bromide 

Downstream Products

• 32507-43-0 (E)/(Z)-1-(buta-1,3-dien-1-yl)-4-chlorobenzene 
• 123372-60-1 2-(4-chloro-phenyl)-3-vinyl-thiirane 

Relevant academic research and scientific papers

Synthesis of Epoxides from Alkyl Bromides and Alcohols with in Situ Generation of Dimethyl Sulfonium Ylide in DMSO Oxidations

Direct conversion of the readily available alkyl bromides and alcohols to value-added epoxides using dimethyl sulfoxide (DMSO) under mild reaction conditions has been developed. Benzyl and allyl bromides, and activated and unactivated alcohols all proceeded smoothly to give epoxides in high to excellent yield. Dimethyl sulfide, generated by DMSO oxidations, was in situ elaborated to form the substituted dimethyl sulfonium ylide species that participates in the Corey-Chaykovsky epoxidation in a domino and one-pot fashion, respectively.

An efficient catalytic ylide route to vinyl epoxides

The ylide epoxidation catalyzed by telluronium salts provides a simple and extremely efficient route to vinyl epoxides in excellent yields. Both aromatic and aliphatic aldehydes work well. The best results were obtained by using 2 mol% of telluronium salts with Cs2CO3 in t-BuOH.

Method used for direct synthesis of epoxy compounds from alcohol

The invention discloses a method used for direct synthesis of an epoxy compounds from an alcohol. According to the method, an alcohol is taken as a raw material, Swern oxidation is adopted to synthesize an aldehyde, a bromo-hydrocarbon and an alkali are added into the aldehyde directly to construct epoxy functional groups, and generate the epoxy compound. According to the method, one-pot method is adopted to realize direct epoxidation of the alcohol, the synthesis route is simple, the preparation process is easy to control, no catalyst is needed in the process, substrate suitable range is wide, reagents are cheap and easily available, preparation conditions are mild, reaction yield is high, and the method is suitable for synthesis of epoxy compounds.

Synthesis of Highly Functionalized Allylic Alcohols from Vinyl Oxiranes and N-Tosylhydrazones via a Tsuji-Trost-Like palladium-Iodide Catalyzed Coupling

An unprecedented efficient palladium(0)-catalyzed reaction of vinyl oxiranes with N-tosylhydrazones, affording skipped allylic alcohols in total regioselectivity and stereoselectivity, with excellent functional-group compatibility, is reported. In this Tsuji-Trost-like allylation, we propose the use of N-tosylhydrazones as a synthetic equivalent of α-styryl anions. More than 20 new products are described, including naturally occurring derivatives. A catalytic system involving an iodide (I-) source is necessary to sustain the catalytic cycle.

Highly regioselective rearrangement of 2-substituted vinylepoxides catalyzed by gallium(III) triflate

Gallium(III) triflate catalyzed the rearrangement of 2-sub-stituted vinylepoxides into β,γ-unsaturated carbonyl compounds with high regio- and chemoselectivity (>97/3) in low catalyst loading (1-5 mol%). The alkyl-substituted trimethylsilylvinyl epoxides

A facile tetrahydrothiophene-catalyzed ylide route to vinyloxiranes

Access to vinyloxiranes using aldehydes and allylic bromides in the presence of 1-5 mol% tetrahydrothiophene is reported. Both aliphatic and aromatic aldehydes work well in this reaction and the catalyst loading could be reduced as low as 0.5 mol%.

New mechanistic aspects on the catalytic transformation of vinylthiiranes to mono and disubstituted 3,6-dihydro-1,2-dithiins by tungsten pentacarbonyl monoacetonitrile

Various alkyl and aryl mono- and disubstituted 3,6-dihydro-1,2-dithiins have been synthesised from their corresponding vinylthiiranes exploiting Adams' tungsten pentacarbonyl monoacetonitrile catalytic transformation. New conclusions pertaining to the rate determining step, the sensitivity of the process to precursor sterics and electronics, and the nature of various reaction intermediates are highlighted.

Simple synthetic method of allyl- and vinyl-epoxides by allylation of carbonyl groups with allylic tins catalyzed by PbI2-HMPA

Allyl epoxides were prepared by the chemoseletive allylation at the carbonyl groups of a-bromo ketones with allylic tin, where PbI2-HMPA effected as a chemoselective catalyst. Moreover, vinyl epoxides were obtained in one pot procedure by the P

Chloroallyl Anion: Highly Regio- and Diastereoselective α-Addition of Chloroallyl Zinc Reagent to Carbonyl Compounds

The chloroallyl zinc reagent generated insitu by deprotonation of allyl chloride in the presence of lithium diisopropylamide and zinc chloride undergoes highly regio- and diastereoselective α-addition to carbonyl compounds to give syn chlorohydrins which

A FIRST EXAMPLE OF CATALYTIC YLIDE EPOXIDATION REACTION: FACILE SYNTHESIS OF VINYL EPOXIDES FROM ALDEHYDES CATALYZED BY DIISOBUTYL TELLURIDE

In the presence of cesium carbonate, a variety of aldehydes can be epoxidized directly with allyl bromide at 50 deg C under solid-liquid phase transfer condition by use of a catalytic amount of diisobutyl telluride to afford vinyl epoxides in good yields