Neuere Methoden der präparativen organischen Chemie V. Organische Synthesen mit Imiden des Schwefeldioxids

Kresze, G.; Wucherpfennig, Wolfgang

doi:10.1002/ange.19670790302

Cited by 129 publications

(12 citation statements)

References 63 publications

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“…The oxaziridines 9 are conveniently prepared by reacting 6 with 7 by heating under reflux in toluene to form 8 [14]. The sulphonylimine 8 is oxidized by 3-chloroperbenzoic acid (M CPBA) or magnesium m onoperoxyphthalate (M gM PP) in a two-phase system (aqueous sodium hydrogen carbonate/ dichlorom ethane) at 20 °C.…”

Section: 4-cl2mentioning

confidence: 99%

2-(4-Toluenesulphonyl)-3-aryloxaziridines as Oxidizing Reagents for P(III) Compounds

Klein

Ugi

1992

Zeitschrift Für Naturforschung B

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The preparation o f four 2-(4-toluenesulphonyl)-3-aryloxaziridines by oxidation o f the cor responding imines by peracids is described. The relative oxidation rates o f trimethyl phosphite by these oxaziridines are determined.Until recently, no generally applicable oxidizing reagents were known for P(III) compounds, al though P(III) com pounds are readily oxidized to form the corresponding P(V) compounds. In 1972, a kinetic study of the deoxygenation of 2-alkyl-3-aryloxaziridines by tributylphosphine was described [9], F or a long time, the oxidation of P(III) com pounds by oxaziridines seems to have been neglected, although there has been consider R,jP + rJX -n-rS -"*"?"? p' -so.- The intermediacy of a phosphorane derivative 3 (R' = OEt; R2=Ph; R 3='Pr) was observed by 31P N M R (Ö = 19.52 ppm, H 3P 0 4) when triethyl phos phite was oxidized by 2 (R 2, R 3 as above) in CDC13[ 11].Recently, the racemates o f diastereom er mix tures of P(III) com pounds were reacted with chiral oxaziridines, and stereoselective destruction [12] of one stereoisomer was observed [13].In the present com m unication we would like to report on the syntheses of 2-(4-toluenesulphonyl)-3-aryloxaziridines (9).These oxaziridines can be used as widely appli cable oxidizing reagents o f P(III) com pounds.

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Section: 4-cl2mentioning

confidence: 99%

2-(4-Toluenesulphonyl)-3-aryloxaziridines as Oxidizing Reagents for P(III) Compounds

Klein

Ugi

1992

Zeitschrift Für Naturforschung B

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“…Wir berichten hier iiber die erste Synthese eines neuen Seleninato-K~mplexes[~] durch SeOl-Insertion in die Eisen-Methyl-Bindung von q'-C5H5Fe(C0)2CH3 (1): Frisch sublimiertes SeOz lost sich in einer gut geruhrten benzolischen Losung von ( I ) vollstandig auf, und gleichzeitig entsteht ein Niederschlag von (2) (2) gegeniiber der der Ausgangsverbindung ( 1 ) zu tieferem Feld kann mit dem elektronegativen Charakter der Seleninatgruppe erklart werden.…”

Section: Selendioxid-einschiebung In Die Eisen-methyl-bindung Von Q5-unclassified

Selendioxid‐Einschiebung in die Eisen‐Methyl‐Bindung von η⁵‐C₅H₅Fe(CO)₂CH₃

Lorenz

1978

Angewandte Chemie

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An (1 0) wird ein Durchschwingen des Triptycen-analogen Geriistteils unter derzu kurzen -Briicke gleichfalls nicht beobachtet, auch nicht beim Erwarmen auf 120°C (bei hoherer Temperatur tritt langsame Zersetzung ein). Auffallig ist noch die Hochfeldverschiebung der zum Stickstoff ortho-standigen Phenylprotonen im N-Phenylmaleinimid-Addukt ( 1 Ob). Nach dem Kalottenmodell sollten diese Protonen jeweils durch Phenylrotation um die C-N-Bindung in den Bereich des abschirmenden Anisotropie-Effekts des darunterliegenden Benzolrings gelangen. Ahnliches zeigt erwartungsgemafi die offenkettige Verbindung ( I 1 ), die analog durch Diels-Alder-Reaktion von 9,lO-Dimethylanthracen mit N-Phenylmaleinimid erhaltlich ist.Weiteren Einblick in die sterischen Verhaltnisse des uberbriickten Triptycensystems ermoglichen Vergleiche rnit den offenkettigen Analoga ( 1 2 ) und (13).

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“…[12] Sharpless and co-workers reported evidence in favor of the initial ene reaction in the selenium dioxide oxidations of alkenes. [13] Several reports on the use of sulfur diimines and N-sulfinyl arenesulfonamides as enophiles were reported by the Kresze, [14] Sharpless [15] and Deleris [16] groups, respectively, but the corresponding products are rather unstable and readily undergo subsequent [2,3]-sigmatropic shift to form CÀN bonds. [17] Interestingly, SO 3 does not undergo the ene reaction, but adds to alkenes at À60 8C to give the corresponding b-sultones.…”

Section: Introductionmentioning

confidence: 99%

BCl₃‐Mediated Ene Reaction of Sulfur Dioxide and Unfunctionalized Alkenes

Marković

Volla

Vogel

et al. 2010

Chemistry A European J

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The first ene reactions of SO(2) and unfunctionalized alkenes are reported. Calculations suggest that the endergonic ene reactions of SO(2) with alkenes can be used to generate beta,gamma-unsaturated sulfinyl and sulfonyl compounds. Indeed, in the presence of one equivalent of BCl(3), the unstable sulfinic acid form stable sulfinic acid.BCl(3) complexes that can be reacted in situ with NCS to generate corresponding sulfonyl chlorides, or with a base to generate corresponding sulfinates. The latter can be reacted with electrophiles to generate sulfones, or with silyl chloride to form beta,gamma-unsaturated silyl sulfinates. The sulfinic acid.BCl(3) complexes can be reacted with ethers that act as oxygen nucleophiles to produce corresponding sulfinic esters. Thus one-pot, three-component synthesis of beta,gamma-unsaturated sulfonamides, sulfinyl esters and sulfones have been developed starting from alkenes and sulfur dioxide (reagent and solvent).

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Neuere Methoden der präparativen organischen Chemie V. Organische Synthesen mit Imiden des Schwefeldioxids

Abstract: Es werden Cycloadditionen und andere Reaktionen vonSpeziell uber diese Anwendung der N-Sulfinylverbindungen wird im folgenden zusammenfassend berichtet. Uber die Reaktivitat der Verbindungen, ihre physikalischen Eigen-

Cited by 129 publications

References 63 publications

2-(4-Toluenesulphonyl)-3-aryloxaziridines as Oxidizing Reagents for P(III) Compounds

2-(4-Toluenesulphonyl)-3-aryloxaziridines as Oxidizing Reagents for P(III) Compounds

Selendioxid‐Einschiebung in die Eisen‐Methyl‐Bindung von η⁵‐C₅H₅Fe(CO)₂CH₃

BCl₃‐Mediated Ene Reaction of Sulfur Dioxide and Unfunctionalized Alkenes

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Neuere Methoden der präparativen organischen Chemie V. Organische Synthesen mit Imiden des Schwefeldioxids

Abstract: Es werden Cycloadditionen und andere Reaktionen vonSpeziell uber diese Anwendung der N-Sulfinylverbindungen wird im folgenden zusammenfassend berichtet. Uber die Reaktivitat der Verbindungen, ihre physikalischen Eigen-

Cited by 129 publications

References 63 publications

2-(4-Toluenesulphonyl)-3-aryloxaziridines as Oxidizing Reagents for P(III) Compounds

2-(4-Toluenesulphonyl)-3-aryloxaziridines as Oxidizing Reagents for P(III) Compounds

Selendioxid‐Einschiebung in die Eisen‐Methyl‐Bindung von η5‐C5H5Fe(CO)2CH3

BCl3‐Mediated Ene Reaction of Sulfur Dioxide and Unfunctionalized Alkenes

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Selendioxid‐Einschiebung in die Eisen‐Methyl‐Bindung von η⁵‐C₅H₅Fe(CO)₂CH₃

BCl₃‐Mediated Ene Reaction of Sulfur Dioxide and Unfunctionalized Alkenes