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C11H15OP requires C, 68.03; H, 7.78%]; Rf (EtOAc/MeOH 20:1) 0.49;
1H NMR (CDCl3, 300 MHz)
: 1.63e1.69 (m, 3H, Me), 2.28e2.51 (m,
4H), 2.61e2.78 (m, 2H), 3.34e3.53 (m, 1H), 5.29e5.44 (m, 1H),
5.58e5.69 (m, 2H), 5.77e5.88 (m, 2H); 13C NMR (CDCl3, 75 MHz)
d
d:
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34.4 (d, JPeC¼65.8 Hz), 35.5 (d, JPeC¼65.5 Hz), 35.5 (d, JPeC¼3.2 Hz),
119.8 (d, JPeC¼9.5 Hz), 127.9 (d, JPeC¼9.8 Hz), 128.7 (d,
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d:
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12. Recently, Birch reduction of aminophosphine-borane was reported, see: (a)
72.34 ppm; GC (Phenomenex Zebron ZB-35HT INFERNO):
tR¼14.45 min; GCeMS (EI, 70 eV) m/z: 194 (1%), 118 (100%), 117
(30%), 103 (15%), 90 (32%).
ꢁ
Reves, M.; Ferrer, C.; Leon, T.; Doran, S.; Etayo, P.; Vidal-Ferran, A.; Riera, A.;
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Verdaguer, X. Angew. Chem., Int. Ed. 2010, 49, 9452e9455; (b) Leon, T.; Riera, A.;
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13. Stankevic, M.; Pietrusiewicz, K. M. Tetrahedron Lett. 2009, 50, 7093e7095.
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L.; McWilliams, J. C.; Ramasamy, D.; Sheppard, R. Org. Lett. 2010, 12, 276e279;
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15. Reduction of diphenylvinylphosphine oxide with 2.5 equiv of sodium in liquid
ammonia afforded cleanly diphenylethylphosphine oxide indirectly confirming
the proposed course of the reaction.
16. Haynes, R. K.; Au-Yeung, T.-L.; Chan, W.-K.; Lam, W.-L.; Li, Z.-Y.; Yeung, L.-L.;
Chan, A. S. C.; Li, P.; Koen, M.; Mitchell, C. R.; Vonwiller, S. C. Eur. J. Org. Chem.
2000, 3205e3216.
Supplementary data
1H, 13C, 31P NMR spectra and GCeMS of compounds. Supple-
mentary data associated with this article can be found in the online
Acknowledgements
Financial support from Polish Ministry of Science and Higher
Education (grant N N204 2328 34) is kindly acknowledged. Authors
are grateful for Dr. Duncan Carmichael for his guidance during the
preparation of manuscript.
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