Solid-liquid Phase Transfer Research Articles

Solid-Liquid Phase-Transfer Catalysis I: Studies of the N-Alkylation of Purines and Pyrimidines

Abstract N-alkylation with acyclic side chains of pyrimidine and purine heterocycles occurs regioselectively at N-1 and N-9 respectively under solid-liquid phase transfer catalysis by 18-crown-6 or tetraglyme in the presence of potassium tert-butoxide at 0°C.

Preparation of 2-Substituted Vinylamino Acid Derivatives

Abstract Solid-liquid phase transfer catalysis in the absence of any added solvent efficiently promotes Michael addition of glycine Schiff bases to phenylvinylsulfoxide. The vinyl group was formed by thermolysis of the phenylsulfinyl function.

Easy and Efficient SNAr Reactions on Halopyridines in Solvent Free Conditions

Solid-liquid phase transfer catalysis (PTC) without added solvent efficiently promotes S N Ar reactions on halopyridines with a variety of anionic nucleophiles generated in situ. This methodology gives access to substituted pyridines in very simplified conditions depending on halide nature. Mechanistic investigations are proposed

Synthesis of unsaturated nitriles via liquid-solid phase transfer catalysis: kinetic study

This study is aimed at the synthesis of unsaturated nitriles, such as 4-pentenonitrile or 3,3-dimethyl-3-butenonitrile. Solid-liquid phase transfer catalysis provides a valuable synthesis route to the preparation of C 5 nitriles. In order to better understand the general reaction mechanism, we have chosen a model reaction: cyanide displacement with 1-chlorobutane using acetonitrile as solvent and 18-crown-6 as transfer agent. Conductimetric results indicates that the 18-crown-6-KCN complex formation and its ionic dissociation are not limiting steps in the displacement reaction. Kinetic studies lead to a second-order rate equation, which can be degenerated into a first-order reaction. The non-linear dependence of the rate constant on the crown ether concentration may be attributed to the effect of complexation-ionisation equilibria. A general discussion of the experimental data obtained is presented.

ChemInform Abstract: Reduction of Allylic Nitro Compounds to Oximes with Carbon Disulfide Under Solid‐Liquid Phase‐Transfer Catalysis Conditions.

ChemInformVolume 21, Issue 38 Preparative Organic Chemistry ChemInform Abstract: Reduction of Allylic Nitro Compounds to Oximes with Carbon Disulfide Under Solid-Liquid Phase-Transfer Catalysis Conditions. D. ALBANESE, D. ALBANESE Centro CNR, Dip. Chim. Org. Ind., Univ., 20133 Milano, ItalySearch for more papers by this authorD. LANDINI, D. LANDINI Centro CNR, Dip. Chim. Org. Ind., Univ., 20133 Milano, ItalySearch for more papers by this authorM. PENSO, M. PENSO Centro CNR, Dip. Chim. Org. Ind., Univ., 20133 Milano, ItalySearch for more papers by this author D. ALBANESE, D. ALBANESE Centro CNR, Dip. Chim. Org. Ind., Univ., 20133 Milano, ItalySearch for more papers by this authorD. LANDINI, D. LANDINI Centro CNR, Dip. Chim. Org. Ind., Univ., 20133 Milano, ItalySearch for more papers by this authorM. PENSO, M. PENSO Centro CNR, Dip. Chim. Org. Ind., Univ., 20133 Milano, ItalySearch for more papers by this author First published: September 18, 1990 https://doi.org/10.1002/chin.199038114Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume21, Issue38September 18, 1990 RelatedInformation

Cobalt Catalysed Carbonylation of Organic Halides under Solid-Liquid Phase Transfer Conditions

Abstract Organic halides are carbonylated under solid liquid phase transfer conditions using Co−(CO)4 as catalyst under CO (1 atmosphere) at 25°C to afford corresponding esters in good yields. No Carbonylation is effected in absence of phase transfer agent (PTA). The striking example is the carbonylation of ethyl haloacetate to diethyl malonate, an important organic intermediate. The parameters such as concentration of PTA, and catalyst and temperature are optimised.

Solid-Liquid Phase Transfer Catalysis Without Solvent: Further Improvement in SNAr Reactions

Abstract Solid-liquid PTC without added solvent efficiently promotes SNAr reactions of a variety of anionic nucleophiles generated in situ. This methodology is applied with success to some examples concerning non-activated aromatic systems. TDA-1 is the most effective catalyst.

Synthesis of α-Aminophospiionic Esters by Solid-Liquid Phase Transfer Catalysis

Abstract (1-aminoalkyl)phosphonic acids are important amino acids with interesting biological properties (1). They are available by various procedures (2). However, a potentially efficient and direct route not very well documented is the use of schiff bases derived from diethyl-aminomethylphosphonate. These substrates have been used to prepare a-alkylated phosphonic aminoacids using strong bases under anhydrous conditions (3). We report here a simple method using solid-liquid phase transfer catalysis (PTC) as wel1 as solid-liquid PTC without solvent:

ChemInform Abstract: Phase-Transfer Catalytic Alkylation of Hydroperoxides: A Convenient Route to Mixed Dialkyl Peroxides.

Abstract The solid-liquid phase transfer catalytic alkylation of hydroperoxides using solid potassium hydroxide as a base and TEBAC as a phase transfer catalyst is reported. When the alkylating agent is a primary bromide, this reaction represents a simple and quick method for the synthesis of mixed dialkyl peroxides in fair yields.

ChemInform Abstract: Synthesis of Diethyl (1‐Aminoalkyl)phosphonates Under Solid‐Liquid Phase‐Transfer Catalysis Conditions.

ChemInformVolume 21, Issue 23 Organoelement Compounds ChemInform Abstract: Synthesis of Diethyl (1-Aminoalkyl)phosphonates Under Solid-Liquid Phase-Transfer Catalysis Conditions. J. P. GENET, J. P. GENET Lab. Synth. Org., Ass. CNRS, Ecole Natl. Sup. Chim., 75231 Paris, FranceSearch for more papers by this authorJ. UZIEL, J. UZIEL Lab. Synth. Org., Ass. CNRS, Ecole Natl. Sup. Chim., 75231 Paris, FranceSearch for more papers by this authorA. M. TOUZIN, A. M. TOUZIN Lab. Synth. Org., Ass. CNRS, Ecole Natl. Sup. Chim., 75231 Paris, FranceSearch for more papers by this authorS. JUGE, S. JUGE Lab. Synth. Org., Ass. CNRS, Ecole Natl. Sup. Chim., 75231 Paris, FranceSearch for more papers by this author J. P. GENET, J. P. GENET Lab. Synth. Org., Ass. CNRS, Ecole Natl. Sup. Chim., 75231 Paris, FranceSearch for more papers by this authorJ. UZIEL, J. UZIEL Lab. Synth. Org., Ass. CNRS, Ecole Natl. Sup. Chim., 75231 Paris, FranceSearch for more papers by this authorA. M. TOUZIN, A. M. TOUZIN Lab. Synth. Org., Ass. CNRS, Ecole Natl. Sup. Chim., 75231 Paris, FranceSearch for more papers by this authorS. JUGE, S. JUGE Lab. Synth. Org., Ass. CNRS, Ecole Natl. Sup. Chim., 75231 Paris, FranceSearch for more papers by this author First published: June 5, 1990 https://doi.org/10.1002/chin.199023240Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume21, Issue23June 5, 1990 RelatedInformation

A Novel Procedure for the Synthesis of Ether-Bridged Perfluoro Non-Ionic Surfactants

Abstract An efficient procedure is described for the synthesis of perfluoro non-ionic surfactants of the type RF-CH 2 (OC 2 H 4)pOH which involves the use of the principle of solid-liquid phase transfer methodology to simplify the Williamson ether synthesis usually employed in previous procedures (5,7).

Phase-Transfer Catalytic Alkylation of Hydroperoxides: A Convenient Route to Mixed Dialkyl Peroxides

Abstract The solid-liquid phase transfer catalytic alkylation of hydroperoxides using solid potassium hydroxide as a base and TEBAC as a phase transfer catalyst is reported. When the alkylating agent is a primary bromide, this reaction represents a simple and quick method for the synthesis of mixed dialkyl peroxides in fair yields.

Microwave Irradiation Plus Solid-Liquid Phase Transfer Catalysis Without Solvent: Further Improvement in Anionic Activation

Abstract Owing to cumulative effects of microwave irradiation and solid-liquid PTC without solvent methodology, conditions for alkylations of potassium acetate by n-octyl or n-cetyl halides are nearly quantitative within 2 minutes on appreciable quantities.

Synthesis of α-Aminophosphonic Esters by Solid-Liquid Phase Transfer Catalysis

Synthesis of α-Aminophosphonic Esters by Solid-Liquid Phase Transfer Catalysis

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°C under solid-liquid phase transfer condition by use of a catalytic amount of diisobutyl telluride to afford vinyl epoxides in good yields with predominant cis stereoselectivity.

Synthesis of Diethyl (1-Aminoalkyl)phosphonates Under Solid-Liquid Phase-Transfer Catalysis Conditions

Alkylations of the stable diethyl N-(diphenylmethylene)aminomethylphosphonate (1) under solid-liquid phase-transfer catalysis (PTC) with or without solvent to give N-(diphenylmethylene) aminomethylphosphonic esters 2 are described. Acidic hydrolysis of 2 afforded diethyl (1-aminoalkyl)phosphonates 3 in good yields

Reduction of Allylic Nitro Compounds to Oximes with Carbon Disulfide under Solid-liquid Phase-Transfer Catalysis Conditions

A mild procedure for the synthesis of allylic oximes 2 from the corresponding nitro derivatives 1, using carbon disulfide as reducing agent in the presence of wet potassium carbonate and a catalytic amount of a phase-transfer agent, is described.

ChemInform Abstract: The Role of Water in Phase‐Transfer Catalysis

Abstract Water is shown to be an essential component in anion exchange process between metal salts and quaternary onium salts in organic solvents. Hydration of ion pairs in organic phases, on the other hand, reduces the nucleophilicity of anions in displacement reactions. These and other effects of water in liquid-liquid and solid-liquid phase transfer catalyzed substitution reactions are combined into the complex role of water in phase transfer catalysis. The subject is discussed in view of some specific examples.

ChemInform Abstract: A Novel Synthesis of 2,3‐Epoxy‐3‐arylpropanol via Arsonium Salt.

Abstract In the presence of KOH(s), β-hydroxyethyltriphenylarsonium bromide 2 reacted directly with aromatic aldehydes at r.t. to give 2,3-epoxy-3-arylpropanol 3 in good yields under solid-liquid phase transfer condition.

Phase-Transfer Catalyzed Monoalkylation of Ethyl 2-(p-Tolylsulfonyl) Acetate

Abstract The facile monoalkylation of ethyl 2-(P-tolylsulfonyl)acetate under solid-liquid phase transfer conditions is reported.