Issue 2, 2001
From the journal:

New Journal of Chemistry

Camphene-derived primary and hydroxymethyl phosphines†

Rebecca A. Berrigan,a   Douglas K. Russell,a   William Henderson,*b   Meto T. Leach,b   Brian K. Nicholson,b   Gary Woodwardc  and  Christopher Harrisc  

* Corresponding authors

a Department of Chemistry, Uniersity of Auckland, Priate Bag, Auckland, New Zealand

b Department of Chemistry, Uniersity of Waikato, Priate Bag, Hamilton, New Zealand
E-mail: w.henderson@waikato.ac.nz
Fax: Fax: +64 7 838 4219

c Rhodia Consumer Specialities Ltd, PO Box 80, Oldbury, West Midlands, UK

Abstract

Thermal disproportionation of (2,2-dimethylbicyclo[2.2.1]hept-3-ylmethyl)phosphinic acid (endo-8-camphanylphosphinic acid, camPO2H2) yields the primary phosphine (2,2-dimethylbicyclo[2.2.1]hept-3-ylmethyl)phosphine (camPH2). The compound has been characterised by NMR spectroscopy, and as its tris(hydroxymethyl)phosphonium chloride salt [camP(CH2OH)3]Cl, synthesised by reaction with excess formaldehyde and hydrochloric acid. The X-ray crystal structure of this phosphonium salt is reported, confirming the endo position of the phosphonium group. On treatment with triethylamine base, camP(CH2OH)3+Cl− is converted to the hydroxymethylphosphine camP(CH2OH)2. The sulfide and selenide of this phosphine have been prepared, together with the platinum(II) complex cis-[PtCl2{camP(CH2OH)2}2]. The gas-phase decomposition of camPH2 has been investigated using the technique of IR laser powered homogeneous pyrolysis. Results indicate the initial elimination of phosphine, followed by the rearrangement and decomposition of camphene through two distinct pathways.

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Article information

DOI
https://doi.org/10.1039/B006252I
Article type
Paper
Submitted
31 Jul 2000
Accepted
04 Oct 2000
First published
21 Dec 2000

New J. Chem., 2001,25, 322-328

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Camphene-derived primary and hydroxymethyl phosphines

R. A. Berrigan, D. K. Russell, W. Henderson, M. T. Leach, B. K. Nicholson, G. Woodward and C. Harris, New J. Chem., 2001, 25, 322 DOI: 10.1039/B006252I

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