Phosphetane

Phosphetane
Names
Preferred IUPAC name
Phosphetane
Identifiers
Properties
C3H7P
Molar mass 74.063 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

A phosphetane[1] is a 4-membered organophosphorus heterocycle. The parent phosphetane molecule, which has the formula C3H7P, is one atom larger than phosphiranes, one smaller than phospholes, and is the heavy-atom analogue of azetidines. The first known phosphetane synthesis was reported in 1957 by Kosolapoff and Struck,[2] but the method was both inefficient and hard to reproduce, with yields rarely exceeding 1%. A far more efficient method was reported in 1962 by McBride,[3] whose method allowed for the first studies into the physical and chemical properties of phosphetanes. Phosphetanes are a well understood class of molecules that have found broad applications as chemical building blocks, reagents for organic/inorganic synthesis, and ligands in coordination chemistry.

  1. ^ Marinetti, Angela; Carmichael, Duncan (2002-01-01). "Synthesis and Properties of Phosphetanes". Chemical Reviews. 102 (1): 201–230. doi:10.1021/cr990135r. ISSN 0009-2665. PMID 11782133.
  2. ^ Kosolapoff, Gennady M.; Struck, Robert F. (1957-01-01). "736. The dissociation constants of some cyclic phosphinic acids". Journal of the Chemical Society (Resumed): 3739–3740. doi:10.1039/JR9570003739. ISSN 0368-1769.
  3. ^ Jungermann, Eric; McBride, J. J.; Clutter, R.; Mais, Ago (February 1962). "A New Phosphorylation Reaction of Olefins. I. Scope of the Reaction". The Journal of Organic Chemistry. 27 (2): 606–610. doi:10.1021/jo01049a063. ISSN 0022-3263.