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vacuum left a pale yellow oil (1.38 g, 82%). δH(400 MHz;
CDCl3) 8.48 (1 H, d, J = 4.0, C6 of C5H4N), 7.5, 7.3 (6 H, 2m,
Ph ϩ C5H4N), 7.10 (1 H, pseudo t, C5H4N), 7.96 (1 H, d,
J = 7.6, C5H4N), 4.88 (1 H, t, J = 4.6 Hz, OCHO), 3.96–3.76
(4 H, m, OCH2CH2O), 3.32 (2 H, s, PCH2C5H4N), 2.0–1.5 (4 H,
m, PCH2CH2); δP(162 MHz; CDCl3) Ϫ19.8, {oxide: 32.6 in
THF–C6D6}; m/z (APCI) 318 (MOHϩ, 100%).
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Methyl 3-[(phenyl)(2-pyridylmethyl)phosphino]propanoate 7.
Methyl acrylate (0.87 g, 10.10 mmol) and AIBN (ca. 0.02g)
in toluene (2 cm3) were added to (phenyl)(2-pyridylmethyl)-
phosphine 66 (1.71 g, 8.50 mmol) in toluene (10 cm3). After
refluxing for 30 minutes, more methyl acrylate (0.25 cm3, 2.8
mmol) and AIBN (ca. 0.01 g in 1 cm3 toluene) were added to
the cooled reaction solution. This step was repeated three more
times after durations of 30, 30 and 60 minutes, leaving to reflux
for 60 minutes after the final addition. The toluene and excess
of methyl acrylate were removed by evaporation under vacuum
to leave a yellow oil of crude compound 7. The product was
purified by dissolution in acetonitrile followed by filtration to
remove a small amount of insoluble material. After removal of
the solvent, the phosphine was subsequently dissolved in diethyl
ether and cooled to Ϫ80 ЊC. This led to precipitation of further
amounts of impurities leaving a solution of 7 of adequate pur-
ity for further use. δH(400 MHz; CD3CN) 8.48 (1 H, d, J = 4.0,
C6 of C5H4N), 7.5 (3 H, m, Ph ϩ C5H4N), 7.35 (3 H, m, Ph),
7.10 (1 H, pseudo t, C5H4N), 7.96 (1 H, d, J = 7.6 Hz, C5H4N),
3.6 (2 H, m, PCH2C5H4N), 3.57 (3 H, s, COOMe), 2.3 (2 H, m,
36 J. Andrieu, B. R. Steele, C. G. Screttas, C. J. Cardin and J. Fornies,
Organometallics, 1998, 17, 839.
37 P. Bhattacharyya, J. Parr and A. M. Z. Slawin, J. Chem. Soc., Dalton
Trans., 1998, 3609.
38 M. Yabuta, S. Nakamura, T. Yamagata and K. Tani, Chem. Lett.,
1993, 323.
CH C᎐O) and 2.0 (2 H, m, PCH ); δ (162 MHz; CDCl ) Ϫ20.5,
᎐
2
2
P
3
(CD3CN) Ϫ14.5 {oxide: 39.1}, (toluene–C6D6) Ϫ20.5 {oxide:
32.1}; m/z (APCI) 304 (MOHϩ, 100%).
39 K. Tani, M. Yabuta, S. Nakamura and T. Yamagata, J. Chem. Soc.,
Dalton Trans., 1993, 2781.
Acknowledgements
40 G. J. P. Britovsek, K. J. Cavell, M. J. Green, F. Gerhards, B. W.
Skelton and A. H. White, J. Organomet. Chem., 1997, 533, 201.
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43 H. Yang, N. Lugan and R. Mathieu, An. Quím. Int. Ed., 1997, 93,
28.
Financial support from the Australian Research Council and
ICI Acrylics (UK) is gratefully acknowledged. We also thank
technical staff of Cardiff University (UK), and the Central
Science Laboratory, University of Tasmania (Australia) for
assistance in the collection of characterisation data.
44 H. Yang, M. Alvarez-Gressier, N. Lugan and R. Mathieu,
Organometallics, 1997, 16, 1401.
45 G. Zhu, M. Terry and X. Zhang, J. Organomet. Chem., 1997, 547,
97.
46 V. D. Romanenko, J.-F. Colom Toro, F. Rivière, J.-G. Wolf and
M. Sanchez, Chem. Commun., 1998, 2183.
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