Reactions of diphenylsulphonium phenacylide

Takaku, M.; Hayasi, Yosio; Nozaki, Hitosi

doi:10.1016/s0040-4020(01)92992-8

Cited by 35 publications

(21 citation statements)

References 10 publications

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“…Thermolysis of the dimedone-derived ylide 39 in aprotic solvents led to rearrangement, 39 Ǟ 41, [70] by way of a five-membered transition state 40. [71] On heating 39 in ethanol, 15% of 41 was formed, along with dime-Scheme 11. Ylides derived from aryl iodides done (42, 10%) and its ethyl ether (43, 32%).…”

Section: Iodonium Ylides and Related Speciesmentioning

confidence: 99%

Carbene Complexes of Nonmetals

Kirmse

2005

Eur J Org Chem

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Electrophilic carbenes accept a variety of n‐ and π‐donors. The products range from persistent ylides to matrix‐isolated xenon complexes. Ylides can be viewed as carbene complexes if they regenerate carbenes thermally or undergo concerted methylene transfer reactions. According to these definitions, the present review focuses on oxonium and iodonium ylides. Transient π‐complexes appear to be involved in addition reactions of carbenes with arenes (but not with alkenes). Nucleophilic carbenes form adducts with Lewis acids which are, for the most part, stable and have been well characterized structurally. Only recently attention has been directed to reversible systems. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Iodonium Ylides and Related Speciesmentioning

confidence: 99%

Carbene Complexes of Nonmetals

Kirmse

2005

Eur J Org Chem

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“…The structure of 13 is tentatively assigned on the grounds of analogous rearrangements observed upon heating of phenyliodonium ylides. 15,16 The yields for the cycloadditions are acceptable for dihydrofuran (35 -78%), but are poor for furan, which is less reactive. The enantioselectivity of the reaction was tested with several Rh(II)-catalysts.…”

Section: Methodsmentioning

confidence: 99%

Selectivity in cyclopropanations and 1,3-cycloadditions in transition metal-catalyzed decompositions of 2-diazocyclohexane-1,3-diones and the corresponding phenyliodonium ylides

Müller¹,

Allenbach²,

Ferri³

et al. 2003

Arkivoc

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The cyclopropanation of olefins with 2-diazodimedone 1a and the corresponding phenyliodonium ylide 1b in the presence of selected chiral Cu(I)-and Rh(II)-catalysts proceeds without significant enantioselectivity. Contrary to previous reports in the literature, the cyclopropanation of styrene with 1a in the presence of [Cu{(+)-facam} 2 ] is not enantioselective. While the transition metal catalyzed 1,3-dipolar cycloaddition of 2-diazodimedone (1a) to furan and dihydrofuran is equally non-selective, the introduction of heteroatoms and/or unsaturation in the carbene precursor results in slightly enhanced enantioselectivity.

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“…Wir sind daher der Meinung, dass diese Umlagerung über einen ipso-Angriff des "negativ geladen" Sauerstoffatoms auf den proximalen "aktivierten" aromatischen Ring verläuft (Schema 4). [27,28] Dieses faszinierende Verhalten zeigte keineswegs nur 4 a; auch seine Analoga konnten problemlos zu den entsprechenden tetra- Tabelle 1: Röntgenographisch ermittelte S-C-Abstände [] sowie R 1 -C-R 2 -und Ph-S-Ph-Winkel [8] …”

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Direkter Ylidtransfer auf Carbonylverbindungen und Heteroarene

2010

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Power‐Transfer: Die Titelreaktion (siehe Schema) verläuft unter milden Bedingungen (Raumtemperatur, kurze Reaktionszeit) und liefert ausgehend von methylenaktiven und heteroaromatischen Verbindungen Sulfonium‐Ylide in einem einzigen Schritt und in sehr hohen Ausbeuten. Ein detaillierter Strukturvergleich einer Vielzahl von Yliden wird genutzt, um den Einfluss der Struktur auf die Reaktivität dieser Verbindungen zu diskutieren.

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Reactions of diphenylsulphonium phenacylide

Cited by 35 publications

References 10 publications

Carbene Complexes of Nonmetals

Carbene Complexes of Nonmetals

Selectivity in cyclopropanations and 1,3-cycloadditions in transition metal-catalyzed decompositions of 2-diazocyclohexane-1,3-diones and the corresponding phenyliodonium ylides

Direkter Ylidtransfer auf Carbonylverbindungen und Heteroarene

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