Triethylammonium Hydroxide Research Articles

Alkaline ILs Supported onto Mesoporous Polymeric 3D Spheres for Catalytic Synthesizing Dimethyl Carbonate in Transesterification

AbstractA novel type of alkyl amine‐based ILs [Et3N]+[OH]− (triethylammonium hydroxide) behaving strong alkali property have been chemically immobilized onto the polymeric 3D spheres with mesoporous structures, spherical morphology and more uniformed active species onto them to form alkali ILs supported 3D polymeric catalysts(3DPs‐ILsOH), which was synthesized via a combined method of substitution with its subsequent anion unites’ exchanging process. The supported 3DPs‐ILsOH catalyzed the transesterification of ethylene carbonate (EC) with methanol, which preferred to exhibit the excellent, efficient activities. At milder reaction temperature of 70 °C within 4.0 h, the conversion of EC achieved to 83.3 % with 99.5 % selectivity of dimethyl carbonate (DMC). Under the same reaction conditions, this type of catalysts could be recovered by a simple filtration and was reused eight times without obvious losing catalytic activities and hardly without any leaching of catalytic species. Its’ catalytic process for generating the chemical of DMC from the CO2 fixation material of EC was studied by using the in‐situ FTIR, and was further verified that the synergetic function roles of triethyl amino cations units with OH− anion units onto the supported catalysts might be one of the important reasons for progressing DMC's yields and its’ catalytic efficiency in transesterification reaction.

Burgess Reagent Facilitated Alcohol Oxidations in DMSO.

The Burgess reagent ([methoxycarbonylsulfamoyl]triethylammonium hydroxide) has historically found utility as a dehydrating agent. Herein we show that, in the presence of dimethyl sulfoxide, the Burgess reagent efficiently and rapidly facilitates the oxidation of a broad range of primary and secondary alcohols to their corresponding aldehydes and ketones in excellent yields and under mild conditions, and can be combined with other transformations (e.g., Wittig olefinations). A mechanism similar to those described for the Pfitzner-Moffatt and Swern oxidations is proposed.

Recent Advances in the Application of the Burgess Reagent in Organic Synthesis

This review focuses on the recent applications of Burgess reagent in the synthesis of organic compounds, with the emphasis, on the total synthesis of natural occurring products. Keywords: Aminoalcohols, Burgess reagent, carbamate, dehydration of alcohols, inner salt, olefination, [methoxycarbonyl-sulfamoyl]triethylammonium hydroxide, sulfamidates.

ChemInform Abstract: A New Method for the Generation of Nitriles from Aldoximes.

Abstract A mild and efficient method for the stereoselective dehydration of α-aldoximes to the corresponding nitriles is described which utilises methyl (carboxysulfamoyl)triethylammonium hydroxide inner salt (Burgess reagent) as the dehydrating agent.

A New Method For The Generation of Nitriles From Aldoximes

A mild and efficient method for the stereoselective dehydration of α-aldoximes to the corresponding nitriles is described which utilises methyl (carboxysulfamoyl)triethylammonium hydroxide inner salt (Burgess reagent) as the dehydrating agent.

ChemInform Abstract: Reactivity of Ethyl‐ and 1‐Phenylethylphosphonic Acid.

AbstractIn the presence of catalytic amounts of triethylammonium hydroxide, the alkylation of the phosphonic acids (I) with the primary alkyl halides (II) leads to the formation of the dialkyl phosphonates (III).

ChemInform Abstract: Hydrostannation of Methyl(carboxysulfamoyl)triethylammonium Hydroxide Inner Salt: A New Route to Tributyltin Isocyanate.

AbstractTributylstannyl isocyanate (III) which is prepared from the inner salt (I) and tributylstannane (II) as mentioned in the title is observed as a by‐product in the formation of vinylic stannanes, e.g. (V), by dehydration of 1‐stannylcycloalkanols such as (IV) with the reagent (I).

Hydrostannation of Methyl (Carboxysulfamoyl) Triethylammonium Hydroxide Inner Salt: A New Route to Tributyltin Isocyanate

Abstract A synthetically useful and facile method for the synthesis of tributyltin isocyanate is described.

ChemInform Abstract: An Efficient Chemoselective Synthesis of Nitriles from Primary Amides.

AbstractThe primary amides (I) are dehydrated with the inner salt of (methoxycarbonylsulfamoyl)triethylammonium hydroxide (Burgess reagent) to form the nitriles (II).

An efficient chemoselective synthesis of nitriles from primary amides

Abstract An efficient chemoselective method for the preparation of nitriles from primary amides is described which utilizes methyl (car☐ysulfamoyl)triethylammonium hydroxide inner salt (Burgess reagent) as the dehydrating reagent.

ChemInform Abstract: RING CONTRACTION OF OLEANDROSE ON THE MACROLIDE ANTIBIOTIC OLEANDOMYCIN WITH ((METHOXYCARBONYL)SULFAMOYL)TRIETHYLAMMONIUM HYDROXIDE INNER SALT

AbstractDas Makrolid (I) reagiert mit dem inneren Salz (II) zu dem Betain (III), das sich thermisch zum Vinyl‐tetrahydrofuran (IVa) umlagert.

Ring contraction of oleandrose on the macrolide antibiotic oleandomycin with [(Methoxycarbonyl)sulfamoyl]triethylammonium hydroxide inner salt.

Ring contraction of the neutral oleandrose sugar in the 14-membered-ring macrolide antibiotic oleandomycin (2) has been accomplished using [(methoxycarbonyl)sulfamoyl]triethylammonium hydroxide inner salt (1). The product of this interesting rearrangement, after methanolic hydrolysis of the 2'-acetate, is the 11-acetyl-3-O-(3"-methoxy-4"-vinylfuranosyl)oleandomycin (12). The in vitro activity of furanoside 12 is only moderately less than that of 11-acetyloleandomycin (13).

Synthesis of 1-phenylseleno-1-vinyl and 1-methylseleno-1-vinyl cyclopropanes by formal dehydration of β-hydroxycyclopropyl selenides

Unknown 1-phenylseleno-1-vinyl and 1-methylseleno-1-vinyl cyclopropanes are readily available from β-hydroxycyclopropyl selenides using (carboxysulfamoyl.) triethylammonium hydroxide inner salt methyl ester. Limitations of the method are presented.

Trans dehydration of alcohols with methyl (carboxysulfamoyl)triethylammonium hydroxide inner salt

Trans dehydration of alcohols with methyl (carboxysulfamoyl)triethylammonium hydroxide inner salt

A New Phosphorylating Reagent. V. The Preparation of α-Glycerophosphoryl Choline and Its Analogues by Means of 2-Chloromethyl-4-nitrophenyl Phosphorodichloridate

β'-Haloethyl isopropylidene-α-glycerophosphoryl 2-chloromethyl-4-nitrophenyl phosphates (10 and 11) were prepared by the stepwise phosphorylations of ethylene halohydrin and 1, 2-isopropylidene-glycerol with 2-chloromethyl-4-nitrophenyl phosphorodichloridate (3), a phosphorylating reagent having an "activatable" protecting group. The protecting group of 10 and 11 was readily and selectively removed by hydrolysis through an active intermediate 14 derived from the reaction of 10 and 11 with various tertiary amines to afford the corresponding isopropylidene-α-glyceryl β'-haloethylhydrogen phosphate (15) along with 2-hydroxy-5-nitrobenzyl trialkyl ammonium chloride (16), a chip of the active intermediate 14. The halogen atom in the ethyl chain of the phosphate 15 reacted with tertiary amine at the same time to afford the corresponding quaternary ammonium compound 17 which was converted by subsequent hydrolysis into α-glycerophosphoryl choline (1a) and its analogues (1b-d). Thus, DL-α-glycerophosphoryl choline (1a), its L-isomer (1a-L), inner salt of β'-(DL-α-glyceryl hydrogen phosphoroxy) ethyl triethyl ammonium hydroxide (1b), 1-[β'-(DL-α-glyceryl) hydrogen phosphoroxy] ethyl 1-methyl piperidinium hydroxide (1c) and inner salt of 1-[β'-(DL-α-glyceryl) hydrogen phosphoroxy] ethyl 1, 4-diazonia bicyclo [2, 2, 2] octane hydroxide (1d) were prepared in good yield. DL-Myristoyl lecithin (18) was prepared by acylation of 1a with myristoyl chloride to confirm the structure of synthetic 1a.