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User:Benjah-bmm27/Oxaphosphetane

From Wikipedia, the free encyclopedia
structure from M. Hamaguchi, Y. Iyamaa, E. Mochizukia, T. Oshimaa, Tetrahedron Lett. (2005) 46, 8949-8952
"First isolation and characterization of 1,2-oxaphosphetanes with three phenyl groups at the phosphorus atom in typical Wittig reaction using cyclopropylidenetriphenylphosphorane"


a rotatable, interactive Jmol model of this molecule is available at my website


Wikipedia coverage

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Basic description

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An oxaphosphetane is a molecule containing a four-membered ring with one phosphorus, one oxygen and two carbon atoms. In a 1,2-oxaphosphetane phosphorus is bonded directly to oxygen. 1,2-Oxaphosphetanes are rarely isolated but are important intermediates in the Wittig reaction and related reactions such as the Seyferth–Gilbert homologation and the Horner–Wadsworth–Emmons reaction.

Similar molecules

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  • oxetane
  • phosphetane
  • 2,2-dihydro-1,2-oxaphosphetane (pentavalent P, parent of Wittig oxaphosphetanes)
  • 1,2-oxaphosphetane (trivalent P)

Sources of information

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VKA, JNH papers on Wittig mechanism

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Journal articles

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  1. 1988: The stereochemistry of Wittig reactions of ylide-anions derived from semi-stabilized phosphonium ylides
  2. 1989: Oxaphosphetane pseudorotation: rates and mechanistic significance in the Wittig reaction
  3. 1994: Synthesis, Structure, and Thermolysis of a 1,5-Dioxa-4λ5-phosphaspiro[3.3]heptane: A Novel Pentacoordinate 1,2-Oxaphosphetane
  4. 1995: Stereoselectivity in the Wittig Reaction of Aromatic Ketones: Origin of Preference for the Olefin Geometry
  5. 1998: Observation of Pseudorotamers of Two Unconstrained Wittig Intermediates, (3RS,4SR)- and (3RS,4RS)-4-Cyclohexyl-2-ethyl-3,4-dimethyl-2,2-diphenyl-1,2λ5-oxaphosphetane, by Dynamic 31P NMR Spectroscopy: Line-Shape Analyses, Conformations, and Decomposition Kinetics
  6. 2002: A Wittig Reaction with 2-Furyl Substituents at the Phosphorus Atom: Improved (Z) Selectivity and Isolation of a Stable Oxaphosphetane Intermediate
    (DOI = 10.1002/1099-0690(200204)2002:7<1143::AID-EJOC1143>3.0.CO;2-G)
  7. 2002: First Isolation and Characterization of an Anti-Apicophilic Spirophosphorane Bearing an Oxaphosphetane Ring: A Model for the Possible Reactive Intermediate in the Wittig Reaction
  8. 2003: Dilithiated phosphazenes: scaffolds for the synthesis of olefins through a new class of bicyclic 1,2-oxaphosphetanes
  9. 2004: Molecular modeling of oxaphosphetane intermediates of wittig olefination reactions
  10. 2007: New possible ionic structures in Wittig reaction: Analysis of stability and rotation barriers by semiempirical PM3 method
  11. 2008: Dynamic NMR study of the oxaphosphetane complexation with lithium during the Wittig reaction

Websites

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