The chemistry of thioethers; differences and analogies with ethers

Брандсма, Л.; Arens, J. F.

doi:10.1002/9780470771075.ch13

Cited by 10 publications

(2 citation statements)

References 118 publications

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“…Direct substitution at the C6 carbon atom of the glucose units having appropriate leaving groups by a dialkyl sulfide bearing a terminal O - or N -nucleophile often lead to an undesired intramolecular substitution . The alternative is a reaction of a cyclodextrin with a sulfide bearing a leaving group, for example, a halogen dialkyl sulfide, which may lead to an undesired cyclic sulfonium intermediate, thus giving rise to a mixture of products .…”

Section: Resultsmentioning

confidence: 99%

Self-Assembled Monolayers of Heptapodant β-Cyclodextrins on Gold

et al. 1998

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A route was developed for the synthesis of three different cyclodextrin adsorbates: heptakis{6-O-[3-(thiomethyl)propionyl)]-2,3-di-O-methyl}-β-cyclodextrin, heptakis{6-O-[12-(thiododecyl)dodecanoyl)]-2,3-di-O-methyl}-β-cyclodextrin (a short and long alkyl chain sulfide cyclodextrin adsorbate, respectively), and heptakis[6-deoxy-6-(3-mercaptopropionamidyl)-2,3-di-O-methyl]-β-cyclodextrin (a short alkyl chain thiol adsorbate). Self-assembled monolayers on gold of these three cyclodextrin adsorbates with seven sulfur moieties were fully characterized by electrochemistry, wettability studies, X-ray photoelectron spectroscopy (XPS), and time-of-flight secondary ion mass spectrometry (TOF-SIMS). The electrochemical capacitance measurements show the differences between the thicknesses of the β-cyclodextrin monolayers, and the XPS-(S2p) measurements show the different effectivenesses of the sulfur moieties of the three monolayers in their binding to the gold surface. Sulfide-based β-cyclodextrin monolayers use on average 4.5 of the 7 attachment points whereas the thiol-based cyclodextrin monolayer only uses 3.2 of the 7 sulfurs. These experiments show that, for adsorbates with multiple attachment points, sulfides may be more effective than thiols. TOF-SIMS measurements confirm the robust attachment of these adsorbates on gold obtained by XPS.

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Section: Resultsmentioning

confidence: 99%

Self-Assembled Monolayers of Heptapodant β-Cyclodextrins on Gold

et al. 1998

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“…50 In addition to alkenes, ethers can also be formed. 43,[51][52][53] The production of ethers from alcohols requires the presence of an acid, and concentrated sulfuric acid is used to produce diethyl ether from ethanol in 95% yield. 52 Diethyl ether is an important solvent and is primarily manufactured by the chemical industry as a by-product of the vapour phase hydration of ethene to ethanol using a supported phosphoric acid catalyst.…”

Section: Alcohols To Alkenes: Brønsted Acid Catalysismentioning

confidence: 99%

Sustainable routes to alkenes: applications of homogeneous catalysis to the dehydration of alcohols to alkenes

Ward

Saccomando²,

Walker³

et al. 2023

Catal. Sci. Technol.

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Das Allopolarisierungs‐Prinzip. Substituenteneinflüsse auf Reaktionen ambifunktioneller Anionen

Gompper¹,

Wagner²

1976

Angewandte Chemie

129

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Die Chemie der ambifunktionellen Anionen ist fir die praparative organische Chernie von grol3er Bedeutung. Um Synthesen planen zu konnen, benotigt man Regeln, die einen Zusammenhang zwischen Struktur und Selektivitat herstellen. Nach dem .,Allopolarisierungs-Prinzip" laOt sich der EinfluB von Substituenten auf kinetisch kontrollierte Reaktionen beschreiben : die Anderungder Selektivitat ist eine Funktion der Anderung der ,,Polaritat'* der ambifunktionellen Anionen. Als ,,Polaritatsindex" dient die relative Ladungsdichte P = lx/ly; X und Y sind die potentiellen reaktiven Zentren. Anhand von Beispielen aus verschiedenen Verbindungsklassen wird versucht, die Brauchbarkeit dieses Prinzips zu demonstrieren.

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The chemistry of thioethers; differences and analogies with ethers

Cited by 10 publications

References 118 publications

Self-Assembled Monolayers of Heptapodant β-Cyclodextrins on Gold

Self-Assembled Monolayers of Heptapodant β-Cyclodextrins on Gold

Sustainable routes to alkenes: applications of homogeneous catalysis to the dehydration of alcohols to alkenes

Das Allopolarisierungs‐Prinzip. Substituenteneinflüsse auf Reaktionen ambifunktioneller Anionen

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