Influence of phase transfer catalyst structure on selectivity

Dehmlow, Eckehard V.

doi:10.1007/bf00696697

Cited by 7 publications

(5 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, C-alkylation of active methylene compounds like activated benzylic nitriles, activated hydrocarbons, and activated ketones under PTC/OH-conditions has been pioneered by Makosza (1975Makosza ( , 1977, and is widely used in a large number of useful organic reactions. Other advantages of these reactions is an increased selectivity in some cases (Dehmlow, 1995). For example, in carbene reactions in the presence of 50% NaOH, hydrolysis of the organic substrate is prevented due to phase separation.…”

Section: Applications Of Ptcmentioning

confidence: 99%

Phase transfer catalysis: Chemistry and engineering

1998

View full text Add to dashboard Cite

Section: Applications Of Ptcmentioning

confidence: 99%

Phase transfer catalysis: Chemistry and engineering

1998

View full text Add to dashboard Cite

“…2-Naphthol (6) was benzylated using a NaOH/PhMe system and a PT catalyst. The yield was 80% (Table 1 / Entry 4) [21]. The sodium salt of 2-naphthol (6) was alkylated using Me 2 SO 4 and Al 2 O 3 /EtOH, but this accomplishment was quite slow (Table 1 / Entry 5) [22].…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Solid-Liquid Phase Alkylation of Naphthols

Bálint

Kovács

Drahos

et al. 2013

LOC

View full text Add to dashboard Cite

Abstract:The microwave promoted alkylation of 1-and 2-naphthols with benzyl, butyl, ethyl and isopropyl halides in the presence of an alkali carbonate may result in O-and C-alkylated products. The alkylations were O-selective in the presence of K 2 CO 3 in acetonitrile as the solvent and in the absence of phase transfer catalyst. The alkylations utilizing butyl and ethyl halides were also O-selective in solventless accomplishment and in the presence of triethylbenzylammonium chloride.

show abstract

“…It is obvious that this ability depends on the nature of the cation of a phase-transfer catalyst Q + and competitive extraction equilibria. Also hydrophilic/lipophilic balance of ion pairs has a significant effect on their extraction capacity [11]. The cation of the catalyst must be sufficiently lipophilic to form ion pairs with anions and effectively moves into the organic phase.…”

Section: Introductionmentioning

confidence: 99%

Study of Extraction Equilibria in the Reaction of Alkaline Hydrolysis of Activated Amino Acid Esters / Badanie Równowag Ekstrakcji W Reakcji Zasadowej Hydrolizy Aktywowanych Estrów Aminokwasów

Doroshkevich

Баранова

Shendrik

et al. 2014

Chemistry-Didactics-Ecology-Metrology

View full text Add to dashboard Cite

Correlation between observed kinetic effects of phase-transfer catalytic reaction of the alkaline hydrolysis of 4-nitrophenyl ester of N-benzyloxycarbonylglycine-4 in the two-phase system chloroform-borate buffer pH = 10 and a content of ionic forms of catalyst was investigated. The phosphonium salts QX (X = Cl¯, Br¯, I¯) shows high catalytic reactivity. Dependence of the reaction kinetics discussed in the framework of the extraction mechanism with a competitive extraction of a nucleophile ОН¯, nucleofuge 4-NO2C6H4O¯ and anion X¯ of the phase-transfer catalyst.

show abstract

Influence of phase transfer catalyst structure on selectivity

Cited by 7 publications

References 26 publications

Phase transfer catalysis: Chemistry and engineering

Phase transfer catalysis: Chemistry and engineering

Microwave-Assisted Solid-Liquid Phase Alkylation of Naphthols

Study of Extraction Equilibria in the Reaction of Alkaline Hydrolysis of Activated Amino Acid Esters / Badanie Równowag Ekstrakcji W Reakcji Zasadowej Hydrolizy Aktywowanych Estrów Aminokwasów

Contact Info

Product

Resources

About