A Novel Method for the Preparation of Tetra-<i>n</i>-butyl-to Tetra-<i>n</i>-octylammonium Hydrogen Sulfates

Dehmlow, Eckehard V.; Vehre, B.; Broda, W.

doi:10.1055/s-1985-31251

Cited by 11 publications

(4 citation statements)

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“…Commercially obtained reagents were used without further purification. The preparation of methyltri- n -octylammonium hydrogensulfate (PTC) is according to the literature. 3a, All reactions were monitored by TLC with Huanghai GF 254 silica gel coated plates. Flash column chromatography was carried out on 300−400 mesh silica gel.…”

Section: Methodsmentioning

confidence: 99%

Oxidation of Benzyl Chlorides and Bromides to Benzoic Acids with 30 Hydrogen Peroxide in the Presence of Na₂WO₄, Na₂VO₄, or Na₂MoO₄ under Organic Solvent-Free Conditions

Shi

Feng

2001

J. Org. Chem.

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Section: Methodsmentioning

confidence: 99%

Oxidation of Benzyl Chlorides and Bromides to Benzoic Acids with 30 Hydrogen Peroxide in the Presence of Na₂WO₄, Na₂VO₄, or Na₂MoO₄ under Organic Solvent-Free Conditions

Shi

Feng

2001

J. Org. Chem.

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“…1) or from tetrabutylammonium thiocyanate 12 by treating it with relatively concentrated sulfuric acid (70%) at 75°C (Scheme 1, eq. 2).…”

Section: Introductionmentioning

confidence: 99%

“…Although TBAHS is commercially available and inexpensive, it can be prepared from tetrabutylammonium azide 11 by treating it with potassium hydrogen sulfate and 10% aqueous sulfuric acid in aqueous medium (Scheme 1, eq. 1) or from tetrabutylammonium thiocyanate 12 by treating it with relatively concentrated sulfuric acid (70%) at 75°C (Scheme 1, eq. 2).…”

Section: Introductionmentioning

confidence: 99%

Tetrabutylammonium Hydrogen Sulfate

Bhattacharyya

2012

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research 2142 spotlight Tetrabutylammonium Hydrogen SulfateCompiled by Aditya Bhattacharyya Aditya Bhattacharyya was born in West Bengal, India in 1986. He graduated in Chemistry from the University of Calcutta in 2006 and received his M.Sc. in 2008 from Bengal Engineering and Science University, Shibpur. Presently, he is working towards his Ph.D. under the supervision of Prof. Manas K. Ghorai in organic chemistry at the Indian Institute of Technology, Kanpur. His research interests focus on the development of novel synthetic methodologies for heterocyclic compounds via S N 2-type ring opening of small ring azaheterocycles with various nucleophiles.

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“…Moreover, the reactions with α -naphthaldehyde and phenanthrene-9-carboxaldehyde under similar conditions exhibited excellent diastereo- and enantioselectivities (entries 4 and 5) . Since ammonium hydrogensulfates can be conveniently prepared from the corresponding bromides without the use of typical anion-exchange resins and simple recrystallization generally provides essentially pure salts, preparation and purification of each chiral ammonium fluoride would no longer be prerequisite. This represents a distinct advantage of our approach for the elaboration of effective chiral quaternary ammonium fluorides, which should play a crucial role in the development of still unexplored fluoride ion-catalyzed asymmetric carbon−carbon bond-forming reactions.…”

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Distinct Advantage of the in Situ Generation of Quaternary Ammonium Fluorides under Phase-Transfer Conditions toward Catalytic Asymmetric Synthesis

2001

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[structure in text] Quaternary ammonium fluorides were found to be efficiently generated in situ from the corresponding ammonium hydrogensulfates by treatment with commercially available potassium fluoride dihydrate (KF.2H(2)O) in THF and directly used as a fluoride source for the generation of carbon nucleophiles from organosilicon compounds. This method can be successfully applied to the preparation of structurally well-defined, C(2)-symmetric chiral quaternary ammonium fluorides of type 1 (X = F), thereby allowing catalytic enantioselective Mukaiyama-type aldol reactions under mild conditions.

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A Novel Method for the Preparation of Tetra-n-butyl-to Tetra-n-octylammonium Hydrogen Sulfates

Cited by 11 publications

References 0 publications

Oxidation of Benzyl Chlorides and Bromides to Benzoic Acids with 30 Hydrogen Peroxide in the Presence of Na₂WO₄, Na₂VO₄, or Na₂MoO₄ under Organic Solvent-Free Conditions

Oxidation of Benzyl Chlorides and Bromides to Benzoic Acids with 30 Hydrogen Peroxide in the Presence of Na₂WO₄, Na₂VO₄, or Na₂MoO₄ under Organic Solvent-Free Conditions

Tetrabutylammonium Hydrogen Sulfate

Distinct Advantage of the in Situ Generation of Quaternary Ammonium Fluorides under Phase-Transfer Conditions toward Catalytic Asymmetric Synthesis

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A Novel Method for the Preparation of Tetra-n-butyl-to Tetra-n-octylammonium Hydrogen Sulfates

Cited by 11 publications

References 0 publications

Oxidation of Benzyl Chlorides and Bromides to Benzoic Acids with 30 Hydrogen Peroxide in the Presence of Na2WO4, Na2VO4, or Na2MoO4 under Organic Solvent-Free Conditions

Oxidation of Benzyl Chlorides and Bromides to Benzoic Acids with 30 Hydrogen Peroxide in the Presence of Na2WO4, Na2VO4, or Na2MoO4 under Organic Solvent-Free Conditions

Tetrabutylammonium Hydrogen Sulfate

Distinct Advantage of the in Situ Generation of Quaternary Ammonium Fluorides under Phase-Transfer Conditions toward Catalytic Asymmetric Synthesis

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Product

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Oxidation of Benzyl Chlorides and Bromides to Benzoic Acids with 30 Hydrogen Peroxide in the Presence of Na₂WO₄, Na₂VO₄, or Na₂MoO₄ under Organic Solvent-Free Conditions

Oxidation of Benzyl Chlorides and Bromides to Benzoic Acids with 30 Hydrogen Peroxide in the Presence of Na₂WO₄, Na₂VO₄, or Na₂MoO₄ under Organic Solvent-Free Conditions