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Base-and/or acid-catalyzed addition of dialkyl phosphites to aldehydes is a recent topic: Simoni, D.; Invidiata, F. P.; Manferdini, M.; Lampronti, I.; Rondanin, R.; Boberti, M.; Pollini, G. P. Tetrahedron Lett. 1998, 39, 7615-7618. Groaning, M. D.; Rowe, B. J.; Spilling, C. D. Tetrahedron Lett. 1998, 39, 5485-5488. Yokomatsu, T.; Yamagishi, T.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1997, 1527-1533. Arai, T.; Bougauchi, M. Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926-2927.
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Pollini, G.P.7
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27
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0032581679
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Base-and/or acid-catalyzed addition of dialkyl phosphites to aldehydes is a recent topic: Simoni, D.; Invidiata, F. P.; Manferdini, M.; Lampronti, I.; Rondanin, R.; Boberti, M.; Pollini, G. P. Tetrahedron Lett. 1998, 39, 7615-7618. Groaning, M. D.; Rowe, B. J.; Spilling, C. D. Tetrahedron Lett. 1998, 39, 5485-5488. Yokomatsu, T.; Yamagishi, T.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1997, 1527-1533. Arai, T.; Bougauchi, M. Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926-2927.
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Spilling, C.D.3
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33748734506
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Base-and/or acid-catalyzed addition of dialkyl phosphites to aldehydes is a recent topic: Simoni, D.; Invidiata, F. P.; Manferdini, M.; Lampronti, I.; Rondanin, R.; Boberti, M.; Pollini, G. P. Tetrahedron Lett. 1998, 39, 7615-7618. Groaning, M. D.; Rowe, B. J.; Spilling, C. D. Tetrahedron Lett. 1998, 39, 5485-5488. Yokomatsu, T.; Yamagishi, T.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1997, 1527-1533. Arai, T.; Bougauchi, M. Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926-2927.
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0029981019
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Base-and/or acid-catalyzed addition of dialkyl phosphites to aldehydes is a recent topic: Simoni, D.; Invidiata, F. P.; Manferdini, M.; Lampronti, I.; Rondanin, R.; Boberti, M.; Pollini, G. P. Tetrahedron Lett. 1998, 39, 7615-7618. Groaning, M. D.; Rowe, B. J.; Spilling, C. D. Tetrahedron Lett. 1998, 39, 5485-5488. Yokomatsu, T.; Yamagishi, T.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1997, 1527-1533. Arai, T.; Bougauchi, M. Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926-2927.
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84953461121
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note
-
There is a byproduct which cannot be removed by distillation from 3a. This byproduct gradually decomposes to PhOH and nonvolatile compounds, which can be removed by distillation. Although acid (2 mol/L HCl) or base (2 mol/L NaOH) treatment of the crude mixture did not promote the decomposition of this byproduct, keeping the crude mixture in the air for a few days and bulb-to-bulb distillation (250 °C/3 mmHg) gave ∼95% pure 3a. (15) The reactions of ethyl and methyl bis(trifluoroethyl)phosphonoacetate with aminoaldehyde were reported. Hensel, M. J.; Fuchs, P. L. Synth. Commun. 1986, 16, 1285-1295.
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31
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0344300723
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note
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For the error margin, it would be safe to think the ratio 86:14 (6.1:1) as 84-88% Z, the ratio 90:10 (9:1) as 89-91% Z, and the ratio 95:5 (19:1) as 94.3-95.7% Z.
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32
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0024422299
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Boeckman, R. K., Jr.; Weidner, C. H.; Perni, R. B.; Napier, J. J. Am. Chem. Soc. 1989, 111, 8036-8037.
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Perni, R.B.4
Napier, J.5
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33
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0015948923
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For the preparation of α,β-unaaturated acids by HWE reaction, see: Koppel, G. A.; Kinnick, M. D. Tetrahedron Lett. 1974, 711-713. Combardo, L.; Taylor, R. J. K. Synthesis 1978, 131-132.
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Koppel, G.A.1
Kinnick, M.D.2
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34
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0011528389
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For the preparation of α,β-unaaturated acids by HWE reaction, see: Koppel, G. A.; Kinnick, M. D. Tetrahedron Lett. 1974, 711-713. Combardo, L.; Taylor, R. J. K. Synthesis 1978, 131-132.
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Synthesis
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Combardo, L.1
Taylor, R.J.K.2
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