Silylations with Bis(trimethylsilyl)acetamide, a Highly Reactive Silyl Donor

Klebe, Johann F.; Finkbeiner, Herman; White, Donald R.

doi:10.1021/ja00966a038

Cited by 386 publications

(96 citation statements)

References 2 publications

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“…In some cases, N,O-bis(trimethy1-silyl) acetamide was added to silylate the OH endgroups, thus avoiding further reaction, such as redistribution,* during heating for GPC analysis. 9 It was not possible to calculate the number of OH groups present by the quantity of Si reagent consumed, since this measure is too sensitive to moisture.…”

Section: Methodsmentioning

confidence: 99%

Comparative gel permeation chromatography calibration techniques in oxidative coupling polymerization

Revillon

Pierre

1970

J of Applied Polymer Sci

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SynopsisGel permeation chromatography was utilized in measuring the kinetics of the oxidative coupling polymerization of 2,bdimethylphenol. The elution c,urves at the early stages of reaction were analyzed by two methods of calibration, specifically by qomparison to the elution times of oligomers up to the bmer level, and by the classical counts method. The two methods give similar results, both indicating a polymerization pattern of the general condensation type and increasing dispersity of molecular weight with degree of polymerization.

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Section: Methodsmentioning

confidence: 99%

Comparative gel permeation chromatography calibration techniques in oxidative coupling polymerization

Revillon

Pierre

1970

J of Applied Polymer Sci

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“…in DMF. [28] Consequently, alternative reagents and conditions have been developed for preparation of TMS ethers of tert-alcohols, [29][30][31][32][33][34] of which the use of (TMS)2NH (0.8 eq. ), iodine (1 mol%) in DMF [35] is amongst the most mild and economic.…”

Section: Entrymentioning

confidence: 99%

Amines vs. N‐Oxides as Organocatalysts for Acylation, Sulfonylation and Silylation of Alcohols: 1‐Methylimidazole N‐Oxide as an Efficient Catalyst for Silylation of Tertiary Alcohols

Murray

Spivey

2015

Adv Synth Catal

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A comparison of the relative catalytic efficiencies of Lewisbasic amines vs. N-oxides for the acylation, sulfonylation and silylation of primary, secondary and tertiary alcohols is reported. Whilst the amines are generally superior to the N-oxides for acylation, the N-oxides are superior for sulfonylation and silylation. In particular, 1-methyl-imidazole-N-oxide (NMI-O) is found to be a highly efficient catalyst for sulfonylation and silylation reactions. To the best of our knowledge, NMI-O is the first amine or N-oxide Lewis basic organocatalyst capable of promoting the efficient silylation of tertalcohols in high yield with low catalyst loading under mild reaction conditions.

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“…tert-Butylcalix [6]arene has been synthesized according to the standard procedure [1]. The pertrimethylsilylation process of both calixarenes is based on the early work of Klebe, Finkbeiner and White using N,O-bis(trimethylsilyl)acetamid as silylating agent [6].…”

Section: Chemicalsmentioning

confidence: 99%

Supramolecular detection of solvent vapours with calixarenes: Mass-sensitive sensors, molecular mechanics and BET studies

Dickert

Schuster

1995

Mikrochim Acta

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Abstract. Chemical sensors, based on highly mass sensitive QMB or SAW devices, coated with thin layers of calixarenes, enable the detection of organic solvent vapours, especially halogenated or aromatic hydrocarbons, down to a few ppm. Force field calculations allow the tailoring of these sensor materials seeing that the predicted interaction energies between the host molecules and a large variety of analytes are linearly correlated to the measured sensor effects. These correlations and also BET adsorption analysis prove the analyte recognition properties of these calixarene coatings to be mainly based on host/guest inclusion principles.Keywords: QMB-SAW-sensors, calixarenes, MM3 force field, BET.Functionalized calixarenes represent an important class of basic skeletons for the synthesis of lipophilic or polar host-systems for the inclusion of favored neutral molecules or ions in solid or liquid state systems [1,2]. The outstanding capacity of the calixarenes as receptors is mainly based on their variable chemical modification potential and their conformational pliability which enables a kind of induced fit on the shape of a suitable guest molecule [3]. Unlike the meanwhile immense number of examples for the detection of ions, there is still a lack of appropriate and powerful sensitive materials and optimized transducer devices for the development of chemical sensors for neutral compounds. The use of supramolecular principles by the application of macrocyclic, enzyme-like calixarenes as sensor coatings on the highly mass sensitive QMB or SAW [4] devices offer promising potentialities [5]. Calixarenes are easy to modify with respect to the shape and size of their cavity and afford a broad potential for development. Due to the fact that QMB and SAW devices are highly sensitive to mass changes of the sensor layer (in the range of 10-9 to 10-t4 g) the systems enable an universal applicability provided analyte molecules are incorporated into the calixarene coatings.

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Silylations with Bis(trimethylsilyl)acetamide, a Highly Reactive Silyl Donor

Cited by 386 publications

References 2 publications

Comparative gel permeation chromatography calibration techniques in oxidative coupling polymerization

Comparative gel permeation chromatography calibration techniques in oxidative coupling polymerization

Amines vs. N‐Oxides as Organocatalysts for Acylation, Sulfonylation and Silylation of Alcohols: 1‐Methylimidazole N‐Oxide as an Efficient Catalyst for Silylation of Tertiary Alcohols

Supramolecular detection of solvent vapours with calixarenes: Mass-sensitive sensors, molecular mechanics and BET studies

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