Phenyl‐schwefelchlorid (II)

Lecher, Hans; Holschneider, F. W.; Köberle, Karl; Speer, Walter; Stöcklin, Paul

doi:10.1002/cber.19250580237

Cited by 74 publications

(31 citation statements)

References 6 publications

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“…Seminal reports of electrophilic sulfenyl group transfer date back to 1925 by Lecher and Stöcklin [10a] who reported the addition of arylsulfenyl chlorides to ethylene (Scheme 1 A). In 1949 the first mechanistic insights from Kharasch and Buess proposed the intermediacy of a 3‐membered, cyclic sulfonium (thiiranium or episulfonium) ion (Scheme 1 B).…”

Section: Historical Background and Development Of Mechanistic Understmentioning

confidence: 99%

Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances

2020

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The last decade has witnessed a burgeoning of new methods for the enantioselective vicinal difunctionalization of alkenes initiated by electrophilic sulfenyl group transfer. The addition of sulfenium ions to alkenes results in the generation of chiral, non‐racemic thiiranium ions. These highly reactive intermediates are susceptible to attack by a myriad of nucleophiles in a stereospecific ring‐opening event to afford anti 1,2‐sulfenofunctionalized products. The practical application of sulfenium ion transfer has been enabled by advances in the field of Lewis base catalysis. This Review will chronicle the initial discovery and characterization of thiiranium ion intermediates followed by the determination of their configurational stability and the challenges of developing enantioselective variants. Once the framework for the reactivity and stability of thiiranium ions has been established, a critical analysis of pioneering studies will be presented. Finally, a comprehensive discussion of modern synthetic applications will be categorized around the type of nucleophile employed for sulfenofunctionalization.

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Section: Historical Background and Development Of Mechanistic Understmentioning

confidence: 99%

Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances

2020

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“…The following compounds were prepared, according to published methods: 1 a±1 c [1], diisopropylchlorophosphine [16], di-tert.-butylchlorophosphine [17], dicyclo-hexylaminodichlorophosphine [18], p-tolylsulfenyl chloride [19]. Other chemicals were commercially available.…”

Section: Methodsmentioning

confidence: 99%

Reactions of N-(N′,N′,N″,N″-tetramethyl)guanidinyl-substituted Phosphines with Organoelement Chlorides involving Phosphorus, Sulfur, and Selenium; Formation of Stable Phosphino-, Thio-, and Selenophosphonium Salts

Münchenberg

Böge

Thönnessen

et al. 1998

Z. anorg. allg. Chem.

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“…Bahnbrechende Arbeiten über den elektrophilen Sulfenylgruppentransfer reichen auf Lecher und Stöcklin [10a] im Jahr 1925 zurück, die über die Addition von Arylsulfenylchloriden an Ethylen berichteten (Schema 1 A). 1949 folgten die ersten mechanistischen Einblicke durch Kharasch uand Buess, die das intermediäre Auftreten eines dreigliedrigen, cyclischen Sulfoniumions (Thiiranium‐ oder Episulfoniumion) postulierten (Schema 1 B).…”

Section: Historischer Hintergrund Und Entwicklung Eines Mechanistischunclassified

Katalytische enantioselektive Sulfenofunktionalisierung von Alkenen: Entwicklung und aktuelle Fortschritte

2020

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Madison mit Arbeiten zur oxidativenDehydrierungl eichter Kohlenwasserstoffe (Gruppe von Ive Hermans). 2017 schloss er sich der Gruppe von S. Denmark an, um enantioselektive Lewis-Base-katalysierte Sulfeniumionentransferprozese zu untersuchen. Scott E. Denmark erhielt 1975 seinen S.B. am MIT und 1980 seinen D.Sc.Tech an der ETH Zürich bei Albert Eschenmoser.Im selben Jahr begann er seine unabhängige Laufbahn an der University of Illinois, und seit 1991 ist er der Reynold C. Fuson Professor of Chemistry.Seine Forschungsinteressen gelten der Entwicklung neuer Synthesen, der explorativen Organoelementchemieu nd dem Ursprung der Stereokontrolle in CC -Bindungsbildungsprozessen.

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Phenyl‐schwefelchlorid (II)

Cited by 74 publications

References 6 publications

Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances

Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances

Reactions of N-(N′,N′,N″,N″-tetramethyl)guanidinyl-substituted Phosphines with Organoelement Chlorides involving Phosphorus, Sulfur, and Selenium; Formation of Stable Phosphino-, Thio-, and Selenophosphonium Salts

Katalytische enantioselektive Sulfenofunktionalisierung von Alkenen: Entwicklung und aktuelle Fortschritte

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