-
2
-
-
0004065126
-
-
2nd ed, American Chemical Society, Washington, DC
-
b) A. D. F. Toy, E. N. Walsh, Phosphorus Chemistry in Everyday Living, 2nd ed., American Chemical Society, Washington, DC, 1987.
-
(1987)
Phosphorus Chemistry in Everyday Living
-
-
Toy, A.D.F.1
Walsh, E.N.2
-
3
-
-
0001433260
-
-
For reviews of the synthesis of phosphoric acid esters, see: a, Eds, B. M. Trost, I. Fleming, E. Winterfeldt, Pergamon, Oxford
-
For reviews of the synthesis of phosphoric acid esters, see: a) Y. Hayakawa in Comprehensive Organic Synthesis, Vol. 6 (Eds.: B. M. Trost, I. Fleming, E. Winterfeldt), Pergamon, Oxford, 1991, pp. 601-630;
-
(1991)
Comprehensive Organic Synthesis
, vol.6
, pp. 601-630
-
-
Hayakawa, Y.1
-
5
-
-
34250704726
-
-
PCT International Application WO 96/17852
-
A. Matsunaga, A. Fujiu, S. Tsuyutani, T. Nozaki, M. Ueda, PCT International Application WO 96/17852, 1996.
-
(1996)
-
-
Matsunaga, A.1
Fujiu, A.2
Tsuyutani, S.3
Nozaki, T.4
Ueda, M.5
-
6
-
-
0033597167
-
-
M. Sprecher, R. Breslow, R. Philosof-Oppenheimer, E. Chavet, Tetrahedron 1999, 55, 5465-5482.
-
(1999)
Tetrahedron
, vol.55
, pp. 5465-5482
-
-
Sprecher, M.1
Breslow, R.2
Philosof-Oppenheimer, R.3
Chavet, E.4
-
9
-
-
0001094491
-
-
For our recent contributions to catalytic direct condensations of carboxylic acids, see: a
-
For our recent contributions to catalytic direct condensations of carboxylic acids, see: a) K. Ishihara, S. Ohara, H. Yamamoto, J. Org. Chem. 1996, 61, 4196-4197;
-
(1996)
J. Org. Chem
, vol.61
, pp. 4196-4197
-
-
Ishihara, K.1
Ohara, S.2
Yamamoto, H.3
-
10
-
-
0034634399
-
-
b) K. Ishihara, S. Ohara, H. Yamamoto, Science 2000, 290, 1140-1142;
-
(2000)
Science
, vol.290
, pp. 1140-1142
-
-
Ishihara, K.1
Ohara, S.2
Yamamoto, H.3
-
11
-
-
16244400119
-
-
c) K. Ishihara, S. Nakagawa, A. Sakakura, J. Am. Chem. Soc. 2005, 127, 4168-4169;
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 4168-4169
-
-
Ishihara, K.1
Nakagawa, S.2
Sakakura, A.3
-
12
-
-
28944444304
-
-
d) A. Sakakura, S. Nakagawa, K. Ishihara, Tetrahedron 2006, 62, 422-433.
-
(2006)
Tetrahedron
, vol.62
, pp. 422-433
-
-
Sakakura, A.1
Nakagawa, S.2
Ishihara, K.3
-
13
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19544374511
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We have reported that nucleophilic bases such as N-butylimidazole promote the condensation of phosphoric acid and alcohols in the presence of tributylamine. However, the catalytic activities of the nucleophilic bases were such that 2 equiv of phosphoric acid and 2 equiv of tributylamine were needed to give phosphoric acid monoesters in good yield: A. Sakakura, M. Katsukawa, K. Ishihara, Org. Lett. 2005, 7, 1999-2002
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We have reported that nucleophilic bases such as N-butylimidazole promote the condensation of phosphoric acid and alcohols in the presence of tributylamine. However, the catalytic activities of the nucleophilic bases were such that 2 equiv of phosphoric acid and 2 equiv of tributylamine were needed to give phosphoric acid monoesters in good yield: A. Sakakura, M. Katsukawa, K. Ishihara, Org. Lett. 2005, 7, 1999-2002.
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14
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0013954717
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Honjo and coworkers have reported the condensation of phosphoric acid with 2′,3′-O-isopropylidene ribonucleosides in the presence of tributylamine. In this work, a large excess of phosphoric acid (5 equiv) and tributylamine (10 equiv) was required. The reactions were conducted at reflux in DMF (b.p. 153°C), and the yields were low (38-58%). Since DMF decomposes gradually at its boiling point, the obtained crude products must be highly contaminated with impurities produced by the decomposition of DMF: M. Honjo, Y. Furukawa, K. Kobayashi, Chem. Pharm. Bull. 1966, 14, 1061-1065.
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Honjo and coworkers have reported the condensation of phosphoric acid with 2′,3′-O-isopropylidene ribonucleosides in the presence of tributylamine. In this work, a large excess of phosphoric acid (5 equiv) and tributylamine (10 equiv) was required. The reactions were conducted at reflux in DMF (b.p. 153°C), and the yields were low (38-58%). Since DMF decomposes gradually at its boiling point, the obtained crude products must be highly contaminated with impurities produced by the decomposition of DMF: M. Honjo, Y. Furukawa, K. Kobayashi, Chem. Pharm. Bull. 1966, 14, 1061-1065.
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15
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0001087127
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The esterification of monosubstituted phosphonic acids has been reported. Monosubstituted phosphonic acids are less acidic than phosphoric acid: Y. R. Dumond, R. L. Baker, J.-L. Montchamp, Org. Lett. 2000, 2, 3341-3344.
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The esterification of monosubstituted phosphonic acids has been reported. Monosubstituted phosphonic acids are less acidic than phosphoric acid: Y. R. Dumond, R. L. Baker, J.-L. Montchamp, Org. Lett. 2000, 2, 3341-3344.
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-
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0000162949
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For a review of oxorhenium(VII) complexes, see: a) C. C. Romão, RE. Kühn, W. A. Herrmann, Chem. Rev. 1997, 97, 3197-3246;
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For a review of oxorhenium(VII) complexes, see: a) C. C. Romão, RE. Kühn, W. A. Herrmann, Chem. Rev. 1997, 97, 3197-3246;
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-
-
-
17
-
-
0034628659
-
-
b) G. S. Owens, J. Arias, M. M. Abu-Omar, Catal. Today 2000, 55, 317-363;
-
(2000)
Catal. Today
, vol.55
, pp. 317-363
-
-
Owens, G.S.1
Arias, J.2
Abu-Omar, M.M.3
-
18
-
-
10044261908
-
-
c) F. E. Kühn, A. Scherbaum, W. A. Herrmann, J. Organomet. Chem. 2004, 689, 4149-4164.
-
(2004)
J. Organomet. Chem
, vol.689
, pp. 4149-4164
-
-
Kühn, F.E.1
Scherbaum, A.2
Herrmann, W.A.3
-
19
-
-
14844283138
-
-
For recent studies on catalysis by oxorhenium(VII) complexes, see: a) C. Morrill, R. H. Grubbs, J. Am. Chem. Soc. 2005, 127, 2842-2843;
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For recent studies on catalysis by oxorhenium(VII) complexes, see: a) C. Morrill, R. H. Grubbs, J. Am. Chem. Soc. 2005, 127, 2842-2843;
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-
-
-
20
-
-
24144454798
-
-
b) P. Paraskevopoulou, N. Psaroudakis, S. Koinis, P. Stavropoulos, K. Mertis, J. Mol. Catal. A 2005, 240, 27-32;
-
(2005)
J. Mol. Catal. A
, vol.240
, pp. 27-32
-
-
Paraskevopoulou, P.1
Psaroudakis, N.2
Koinis, S.3
Stavropoulos, P.4
Mertis, K.5
-
23
-
-
26444564226
-
-
e) F. M. Pedro, S. Hirner, F. E. Kühn, Tetrahedron Lett. 2005, 46, 7777-7779.
-
(2005)
Tetrahedron Lett
, vol.46
, pp. 7777-7779
-
-
Pedro, F.M.1
Hirner, S.2
Kühn, F.E.3
-
24
-
-
0004204702
-
-
3rd ed, Clarendon, Oxford
-
J. Emsley, The Elements, 3rd ed., Clarendon, Oxford, 1998, pp. 172-173.
-
(1998)
The Elements
, pp. 172-173
-
-
Emsley, J.1
-
25
-
-
33750298803
-
-
K. Ishihara, Y. Furuya, H. Yamamoto, Angew. Chem. 2002, 114, 3109-3112;
-
(2002)
Angew. Chem
, vol.114
, pp. 3109-3112
-
-
Ishihara, K.1
Furuya, Y.2
Yamamoto, H.3
-
26
-
-
0037119319
-
-
Angew. Chem. Int. Ed. 2002, 41, 2983-2986.
-
(2002)
Chem. Int. Ed
, vol.41
, pp. 2983-2986
-
-
Angew1
-
27
-
-
19544377371
-
-
A. Sakakura, R. Kondo, K. Ishihara, Org. Lett. 2005, 7, 1971-1974.
-
(2005)
Org. Lett
, vol.7
, pp. 1971-1974
-
-
Sakakura, A.1
Kondo, R.2
Ishihara, K.3
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34250716411
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In our previous work, 6] a 1:1 mixture of DMF and EtNO2 was used as solvent. Since phosphoric acid is not soluble in this mixture, 1 equiv of tributylamine was required to dissolve the phosphoric acid and promote the reaction
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2 was used as solvent. Since phosphoric acid is not soluble in this mixture, 1 equiv of tributylamine was required to dissolve the phosphoric acid and promote the reaction.
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34250791226
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Igepal CO-210 (purchased from Aldrich) is a mixture of isomers. A representative structure of Igepal CO-210 is shown in Table 2.
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Igepal CO-210 (purchased from Aldrich) is a mixture of isomers. A representative structure of Igepal CO-210 is shown in Table 2.
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34250735540
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Acid-sensitive alcohols might be converted into the corresponding phosphoric acid monoesters in the presence of one or more equivalents of dibutylamine
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Acid-sensitive alcohols might be converted into the corresponding phosphoric acid monoesters in the presence of one or more equivalents of dibutylamine.
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31
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0001638530
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3 and alcohols: W. A. Herrmann, W. A. Wojtczak, G. R. J. Artus, F. E. Kühn, M. R. Mattner, Inorg. Chem. 1997, 36, 465-471.
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3 and alcohols: W. A. Herrmann, W. A. Wojtczak, G. R. J. Artus, F. E. Kühn, M. R. Mattner, Inorg. Chem. 1997, 36, 465-471.
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32
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34250712263
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31P NMR spectroscopy.
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31P NMR spectroscopy.
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33
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37049048425
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N. Bailey, A. Carrington, K. A. K. Lott, M. C. R. Symons, J. Chem. Soc. 1960, 290-297.
-
(1960)
J. Chem. Soc
, pp. 290-297
-
-
Bailey, N.1
Carrington, A.2
Lott, K.A.K.3
Symons, M.C.R.4
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34250738886
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When the reaction was conducted in the absence of alcohols, pyrophosphoric acid (5) was produced in about 30% yield
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When the reaction was conducted in the absence of alcohols, pyrophosphoric acid (5) was produced in about 30% yield.
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