25709-55-1

Usage

Type of compound

Quaternary ammonium salt

Function

Phase transfer catalyst in organic synthesis

Application

Used in reactions involving the transfer of anionic species between immiscible phases

Specific use

Commonly employed in reactions that occur in organic solvents and aqueous solutions

Structural feature

Quaternary ammonium structure

Role of structure

Allows effective transport of reactants from one phase to another

Importance

Essential tool in the realm of organic chemistry

InChI:InChI=1/C8H15O2S.BrH/c1-2-10-8(9)7-11-5-3-4-6-11;/h2-7H2,1H3;1H/q+1;/p-1

Upstream product

• 110-01-0 thiophene 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 4561-70-0 furyl-1 carboxyethoxy-2 oxirane 
• 4561-70-0 2,3-Epoxy-3-<2>furyl-propionsaeure-aethylester 
• 75755-52-1 trans-ethyl 3-(4-chlorophenyl)oxirane-2-carboxylate 
• 109318-46-9 ethyl 3-(3-nitrophenyl)glycidate 
• 16546-01-3 ethyl 3-(4-methoxyphenyl)-2,3-epoxypropionate 
• 134176-18-4 (+/-)-(1S,5R,6S)-ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate 
• 134176-18-4 (±)-ethyl (1S,5R,6R)-2-oxobicyclo[3.1.0]hexane-6-carboxylate 
• 1619239-41-6 1-(2-ethoxy-2-oxoethyl)tetrahydro-1H-thiophen-1-ium tetraphenylborate 
• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 
• 121-39-1 ethyl 3-phenylglycidate 
• 52788-71-3 ethyl 3-(4-methylphenyl)oxirane-2-carboxylate 
• 109844-94-2 ethyl 3-(4-nitrophenyl)oxirane-2-carboxylate 

Relevant academic research and scientific papers

Towards a General Understanding of Carbonyl-Stabilised Ammonium Ylide-Mediated Epoxidation Reactions

The key factors for carbonyl-stabilised ammonium ylide-mediated epoxidation reactions were systematically investigated by experimental and computational means and the hereby obtained energy profiles provide explanations for the observed experimental results. In addition, we were able to identify the first tertiary amine-based chiral auxiliary that allows for high enantioselectivities and high yields for such epoxidation reactions.

COMPOUNDS AND METHODS for the inhibition of HDAC

Disclosed are compounds having the formula: wherein X1, X2, X3, R1, R2, R3, R4, Y, A, Z, L and n are as defined herein, and methods of making and using the same.

Metal-free carbon-carbon cross-couplings between the ion pairs in sulfonium tetraphenylborates

A series of sulfonium tetraphenylborates can be readily prepared by the metathesis of sulfonium halides with sodium tetraphenylborates. After heating at 120-150 °C, the sulfonium tetraphenylborates can smoothly undergo the cross-couplings between the tetraphenylborate anions and the sulfonium cations in the absence of a metal catalyst. For carbonylmethyl-, benzyl-, and allylsulfoniums, the corresponding carbonylmethyl-phenyl, benzyl-phenyl, and allyl-phenyl cross-coupling products can be obtained in 22-76% yields. An interionic electron-transfer mechanism for this cross-coupling reaction is proposed.

PROCESS FOR THE SYNTHESIS OF SUBSTITUTED PYRAZOLES

A process for the preparation of 4,5-di- and 2,4,5-trisubstituted pyrazole 3-carboxylates from 3-acyloxirane-2-carboxylates and hydrazine compounds.

CYCLOPROPYL-CONTAINING POLYAMINE ANALOGS AS DISEASE THERAPIES

This disclosure relates to specific polyamine analogs and methods of treating cancer using polyamine analogs. The polyamine analogs have cyclopropyl groups in their internal segments.

Preparation of chiral cyclopropanes with a carbohydrate fragment from levoglucosenone

Levoglucosenone (a chiral α,β-unsaturated ketone derivative of cellulose) underwent stereoselective cyclopropanation with sulfonium ylides to form chiral trisubstituted cyclopropanes annulated with the carbohydrate moiety in high yields.

Asymmetric sulfonium ylide mediated cyclopropanation: Stereocontrolled synthesis of (+)-LY354740

The reaction of ester-stabilized sulfonium ylides with cyclopentenone to give (+)-5 ((1S,5R,6S)-ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate), an important precursor to the pharmacologically important compound (+)-LY354740, has been studied using chiral sulfides operating in both catalytic (sulfide, Cu(acac)2, ethyl diazoacetate. 60°C) and stoichiometric modes (sulfonium salt, base, room temperature). It was found that the reaction conditions employed had a major influence over both diastereo- and enantio-selectivity. Under catalytic conditions, good enantioselectivity with low diastereoselectivity was observed, but under stoichiometric conditions low enantioselectivity with high diastereoselectivity was observed. When the stoichiometric reactions were conducted at high dilution, diastereoselectivity was reduced. This indicated that base-mediated betaine equilibration was occurring (which is slow relative to ring closure at high dilution). Based on this model, conditions for achieving high enantioselectivity were established as follows: use of a preformed ylide, absence of base, hindered ester (to reduce ylide-mediated betaine equilibration), and low concentration. Under these conditions high enantioselectivity (95% ee) was achieved, albeit with low diastereocontrol. Our model for selectivity has been applied to other sulfonium ylide mediated cyclopropanation reactions and successfully accounts for the diastereoselectivity observed in all such reported reactions to date.

Epoxide Synthesis in Interfacial Solid-Liquid Conditions

In this paper an analysis of the factors responsible for discrimination among differing structures of organic reagents by the microcrystalline structure of solids is presented.As a vehicle of this study, the epoxide synthesis using three sulfur ylide precursors (sulfonium and sulfoxonium salts) and four microcrystalline solids was investigated.Neither the surface area nor the number of active sites at the solid surface control the epoxide yield.It appears that the cell lattice of the solid determines the ylide structure, its nucleophilicity, and thus the reaction yield.

Ba(OH)2 AS CATALYST IN ORGANIC REACTIONS - PART XIX - STRUCTURE-CATALYTIC ACTIVITY RELATIONSHIP IN THE AdN OF SEVERAL YLIDS TO CH=O GROUP, CATALYZED BY ACTIVATED BARIUM HYDROXIDE CATALYST

The reactivity of several products R1R2CH-X(1+), 1, (X=N,P,S), which can produce ylids by reaction with bases, has been tested using the activated barium hydroxide catalysts, C-200.Wittig-Horner, Wittig, Corey-Chaykovsky and Kroehnke type reactions have been analyzed.The pKa of 1, and the structure of active sites control the process.When 1 has a strong acid character, the process takes place - dissolving the solid - in homogeneous phase.When 1, has pKa values 11.7), that control the reaction mechanism and the reactivity of adsorbed ylids.

EPOXYDATION EM MILIEU HETEROGENE SOLIDE-LIQUIDE FAIBLEMENT HYDRATE : ETUDE DE LA REACTION AUTOUR DE LA STRUCTURE DU SEL DE SULFONIUM

Epoxide formation by sulphur ylid insertion into aldehydes under heterogeneous conditions in the presence of small quantities of water is described.Trimethylsulphonium and S-methylthiolanium bromide and iodide have been studied.For all alkyl substituents the bromide gives better results than the iodide, this is interpreted in terms of the reaction mechanisms.Under optimum conditions high yields of epoxides are obtained.