Synthese und Reaktionen der P‐Halogen‐phosphonium‐ylide, R2P(X)=CR2
- 1 November 1989
- journal article
- research article
- Published by Wiley in Zeitschrift für Chemie
- Vol. 29 (11) , 396-405
- https://doi.org/10.1002/zfch.19890291103
Abstract
P Halogeno phosphonium ylides are readily available reagents possessing high activity and various chemical properties. Several methods exist for the synthesis of P halogeno phosphonium ylides: reaction of tertiary phosphines with carbon tetrachloride, dehydro‐halogenation of phosphonium salts, and halogenotropic rearrangement of α‐halogenoalkylphosphines. The interaction of P halogeno phosphonium ylides with carbonyl Compounds yields [2 + 2] ‐cycloaddition products which, depending on their structure, decompose to form allylphosphonates, vinylphosphonates, organophosphorus ketens, thioketens or ketenimines. P Halogeno phosphonium ylide posses a high phosphorylating ability. Their P=C double bond readily adds different nucleophiles, containing mobile hydrogen to form phosphonium salts. The reversible migrations of the chlorine atom from α‐carbon atom to the phosphorus atom proceeding with the change of phosphorus coordination number PIV ⇌ PIII are typical for P halogeno phosphonium ylides.Keywords
This publication has 23 references indexed in Scilit:
- Synthesis and reactivity of diazomethylenephosphoranes (P=C=N2). New phosphacumulene ylides and first stable pseudo-unsaturated diazo derivativesJournal of the American Chemical Society, 1987
- NITROGEN, PHOSPHORUS, SULFUR–BUILDING STONES OF RINGS AND CAGESPhosphorus and Sulfur and the Related Elements, 1986
- Zur Umsetzung des Zweikomponentensystems Trialkylphosphit/ Tetrachlorkohlenstoff mit wasserstoffhaltigen Nucleophilen 2. Die Reaktion mit Ammoniak und AminenZeitschrift für anorganische und allgemeine Chemie, 1985
- Neue phosphororganische Verbindungsklassen auf der Basis von Halogenderivaten des dreibindigen PhosphorsZeitschrift für Chemie, 1984
- Bildung siliciumorganischer Verbindungen. 96. Bildung und Struktur von P‐Yliden des 1,3,5‐Trisilacyclohexans (Einfluß der Substituenten)Zeitschrift für anorganische und allgemeine Chemie, 1984
- P ‐Chlor‐alkylidenphosphorane und (α‐Chloralkyl)phosphane, durch 1,2‐Chlorverschiebung ineinander überführbare StrukturisomereEuropean Journal of Inorganic Chemistry, 1983
- Bis(chlordiphenylphosphorandiyl)methanAngewandte Chemie, 1979
- A New Synthesis of 1,1-Dibromoölefins via Phosphine-Dibromomethylenes. the Reaction of Triphenylphosphine with Carbon TetrabromideJournal of the American Chemical Society, 1962
- Über Additionsprodukte von Trialkylphosphinen, ‐arsinen und ‐stibinenEuropean Journal of Inorganic Chemistry, 1907
- IV. On the effects produced in human blood-corpuscles by sherry wine, &cProceedings of the Royal Society of London, 1860