Diels alder reactions of P-chloro (bistrimethylsilyl) methylene phosphine

Abbari, M.; Cosquer, P.; Tonnard, F.; Ko, Y. Y. C. Y. L.; Carrié, R.

doi:10.1016/0040-4020(91)80009-q

Cited by 16 publications

(7 citation statements)

References 43 publications

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“…Yields determinated by NMR spectroscopy with an internal reference were greater than 70% (purity > 90%). The characterisation was supported by HRMS and 31 P, 1 H and 13 C NMR data, all of which were consistent with the assigned structure. ‡ We have shown in our previous work that (i) transient phosphaalkenes are detectable by 31 P NMR spectroscopy in the dehydrochlorination of primary and secondary a-chloroalkylphosphines 2d,5 under controlled temperature conditions (from 280 to 20 °C) and (ii) polymerisation of the chlorophosphaalkene intermediates was observed in the elimination of HCl from a,aA-dichlorophosphines by a weak Lewis base (pyridine) in the absence of a trapping agent.…”

supporting

confidence: 59%

“…The relative configuration at P and C(8) of 5c was established on the basis of the 2 J PC(7) coupling constant: the observed value (15 Hz) favours a trans relationship between the lone pair and C(7). 3,13,14 § (ii) The cis-fused cycloadduct is proposed to take into account the preference of the P-substituent for the endo postions. 2a,15,16 The phenyl and chloride substituents in 4c are consequently in a trans relationship.…”

mentioning

confidence: 99%

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Intramolecular [4 + 2] cycloadditions involving transient phosphaalkene intermediates as dienophiles: a useful entry to phosphabicyclo[4.3.0]non-4-ene derivatives

Pilard¹,

Friot²,

Denis³

1998

Chem. Commun.

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supporting

confidence: 59%

mentioning

confidence: 99%

Intramolecular [4 + 2] cycloadditions involving transient phosphaalkene intermediates as dienophiles: a useful entry to phosphabicyclo[4.3.0]non-4-ene derivatives

Pilard¹,

Friot²,

Denis³

1998

Chem. Commun.

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“…[54] Diels-Alder [4þ2] cycloadditions have also been studied in some detail. [55] In most cases, the Woodward-Hoffmann rules are respected, although some exceptions have been recorded. For example, all four possible isomers have been obtained in the reaction of a pure isomer of 9 with 2,3-dimethyl-1,3-butadiene [Eq.…”

Section: Reactivitymentioning

confidence: 94%

Phospha‐Organic Chemistry: Panorama and Perspectives

2003

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Since the beginning of the seventies, organophosphorus chemistry has been completely rejuvenated by the discovery of stable derivatives in which phosphorus has the coordination numbers one or two. The chemistry of these compounds mimics the chemistry of their all-carbon analogues. In this Review article this analogy is discussed for the phosphorus counterparts of alkenes, alkynes, and carbenes. In each case, the synthesis, reactivity, and coordination modes are briefly examined. Some special electronic configurations are also discussed, which include one-electron Pbond;P bonds, strained bonds, and aromatic systems. To conclude, some potential applications of this chemistry in the areas of molecular materials and homogeneous catalysis are presented.

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“…Diels‐Alder‐[4+2]‐Cycloadditionen wurden ebenfalls detailliert untersucht 55. In den meisten Fällen verlaufen sie nach den Woodward‐Hoffmann‐Regeln, allerdings wurden auch einige Ausnahmen verzeichnet.…”

Section: Phosphaalkeneunclassified

Phosphaorganische Chemie: Panorama und Perspektiven

Mathey

2003

Angewandte Chemie

198

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Die gesamte phosphororganische Chemie wurde mit Beginn der siebziger Jahre infolge der Entdeckung stabiler phosphororganischer Derivate mit Koordinationszahlen des Phosphors von 1 oder 2 aufgefrischt. Bezüglich ihrer Chemie gleichen diese Verbindungen ihren reinen Kohlenstoff‐Analoga. Dieser Aufsatz widmet sich der Analogie zwischen den Phosphorderivaten und den entsprechenden Alkenen, Alkinen und Carbenen, wobei jede Verbindungsklasse anhand ihrer Synthese, ihrer Reaktivität und ihres Koordinationstyps kurz vorgestellt wird. Des Weiteren werden besondere Elektronenkonfigurationen der Phosphorverbindungen behandelt, darunter P‐P‐Einelektronenbindungen, gespannte Bindungen und aromatische Systeme. Abschließend wird auf mögliche Anwendungen dieser Chemie zur Herstellung molekularer Materialien und in der homogenen Katalyse verwiesen.

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Diels alder reactions of P-chloro (bistrimethylsilyl) methylene phosphine

Cited by 16 publications

References 43 publications

Intramolecular [4 + 2] cycloadditions involving transient phosphaalkene intermediates as dienophiles: a useful entry to phosphabicyclo[4.3.0]non-4-ene derivatives

Intramolecular [4 + 2] cycloadditions involving transient phosphaalkene intermediates as dienophiles: a useful entry to phosphabicyclo[4.3.0]non-4-ene derivatives

Phospha‐Organic Chemistry: Panorama and Perspectives

Phosphaorganische Chemie: Panorama und Perspektiven

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