17
(160 mg, 1.26 mmol). After stirring at room temperature for
15 h, the deep orange-red mixture was evaporated to dryness
under reduced pressure, extracted into dichloromethane (35 mL)
and flash chromatographed in dichloromethane : pentane
1 : 9 on neutral alumina. Evaporation of the red band gave
the product 20 as a deep orange-red powder, showing data in
full accordance with precedent32 (174 mg, 62%).
A solution of [FeCp*(TMEDA)Cl]30 (4.1 g, 12.0 mmol) in
THF (100 mL) was added by a cannula over a period of 5 min
to a DME (100 mL) solution of potassium 2,5-dimethoxy-
carbonyl-3,4-dimethylphospholideꢃ0.75 THF 2Me (4 g,
12.5 mmol). The deep red solution was stirred for an hour at
room temperature and then treated with a methanol (1 mL)
solution of 2,20-bipyridine (500 mg, 8.9 mmol). The violet
precipitate was discarded, and the solution was purified by
rapid chromatography on silica in ethyl acetate. Evaporation
to dryness gave the product as a red solid (3.45 g, 69%).
31P NMR (C6D6): ꢁ30.4 ppm. 1H NMR (C6D6): 3.41
(s, 6H, OMe), 2.62 (s, 6H, Me), 1.53 (s, 15H, Cp*) ppm.
13C NMR (C6D6): 171.9 (d, JCP = 18.4 Hz, CO2Me), 98.6 (d,
JCP = 6.4 Hz, PCCMe), 84.8 (Cp*), 83.2 (d, JCP = 58.4 Hz,
PC), 50.8 (OMe), 12.3 (PCCMe), 9.2 (Cp*Me) ppm. CI-MS
(m/z, %): 419 ([M + H]+, 100%) HRMS: calculated for
C20H27FeO4 P: 418.0996, found: 418.0998. Elemental analysis:
required for C20H27PO4Fe: C, 57.43; H, 6.51; found C, 57.80;
H, 6.57%.
Acknowledgements
We thank CNRS and the Ecole Polytechnique, Palaiseau,
(AMX grant to EM) for financial support. We are also grateful
to Antoine Buchard (Polytechnique) for a small sample of
[Fe(MeCN) (BF ) ] and Dr Jurgen Klankermayer for some
¨
6
4 2
preliminary work in this area.
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31P NMR (THF): ꢁ19.9 ppm. H NMR (C6D6): 3.37 (6H,
2 OMe), 2.19 (6H, 2Me), 1.57 (15H, Cp*) ppm. 13C NMR
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ꢀc
This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2010
1346 | New J. Chem., 2010, 34, 1341–1347