-
1
-
-
0000434277
-
-
For reviews, see: a
-
For reviews, see: a) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal. 2001, 343, 393-427;
-
(2001)
Adv. Synth. Catal
, vol.343
, pp. 393-427
-
-
Ishii, Y.1
Sakaguchi, S.2
Iwahama, T.3
-
4
-
-
0036738419
-
-
d) R. A. Sheldon, I. W. C. E Arends, G.-J. Brink, A. Dijksman, Acc. Chem. Res. 2002, 35, 774-781;
-
(2002)
Acc. Chem. Res
, vol.35
, pp. 774-781
-
-
Sheldon, R.A.1
Arends, I.W.C.E.2
Brink, G.-J.3
Dijksman, A.4
-
5
-
-
56449118219
-
-
e) C. Galli, P. Gentili, O. Lanzalunga, Angew. Chem. 2008, 120, 4868-4874;
-
(2008)
Angew. Chem
, vol.120
, pp. 4868-4874
-
-
Galli, C.1
Gentili, P.2
Lanzalunga, O.3
-
6
-
-
53549097389
-
-
Angew. Chem. Int. Ed. 2008, 47, 4790-4796;
-
(2008)
Angew. Chem. Int. Ed
, vol.47
, pp. 4790-4796
-
-
-
9
-
-
44049092112
-
-
Angew. Chem. Int. Ed. 2008, 47, 3506-3523.
-
(2008)
Angew. Chem. Int. Ed
, vol.47
, pp. 3506-3523
-
-
-
10
-
-
39049159714
-
-
For examples in medicinal chemistry, see: a
-
For examples in medicinal chemistry, see: a) M. L. McKee, S. M. Kerwin, Bioorg. Med. Chem. 2008, 16, 1775-1783;
-
(2008)
Bioorg. Med. Chem
, vol.16
, pp. 1775-1783
-
-
McKee, M.L.1
Kerwin, S.M.2
-
11
-
-
38049160718
-
-
b) E. Oksuzoglu, O. Temiz-Arpaci, B. Tekiner-Gulbas, H. Eroglu, G. Sen, S. Alper, I. Yildiz, N. Diril, E. Aki-Sener, I. Yalcin, Med. Chem. Res. 2008, 16, 1-14;
-
(2008)
Med. Chem. Res
, vol.16
, pp. 1-14
-
-
Oksuzoglu, E.1
Temiz-Arpaci, O.2
Tekiner-Gulbas, B.3
Eroglu, H.4
Sen, G.5
Alper, S.6
Yildiz, I.7
Diril, N.8
Aki-Sener, E.9
Yalcin, I.10
-
12
-
-
33746077081
-
-
c) S.-T. Huang, I.-J. Hsei, C. Chen, Bioorg. Med. Chem. 2006, 14, 6106-6119;
-
(2006)
Bioorg. Med. Chem
, vol.14
, pp. 6106-6119
-
-
Huang, S.-T.1
Hsei, I.-J.2
Chen, C.3
-
13
-
-
30444437324
-
-
d) C. G. Mortimer, G. Wells, J.-P. Crochard, E. L. Stone, T. D. Bradshaw, M. F. G. Stevens, A. D. Westwell, J. Med. Chem. 2006, 49, 179-185;
-
(2006)
J. Med. Chem
, vol.49
, pp. 179-185
-
-
Mortimer, C.G.1
Wells, G.2
Crochard, J.-P.3
Stone, E.L.4
Bradshaw, T.D.5
Stevens, M.F.G.6
Westwell, A.D.7
-
14
-
-
20944432343
-
-
e) M. C. Van Zandt, M. L. Jones, D. E. Gunn, L. S. Geraci, J. H. Jones, D. R. Sawicki, J. Sredy, J. L. Jacot, A. T. DiCioccio, T. Petrova, A. Mitschler, A. D. Podjarny, J. Med. Chem. 2005, 48, 3141-3152;
-
(2005)
J. Med. Chem
, vol.48
, pp. 3141-3152
-
-
Van Zandt, M.C.1
Jones, M.L.2
Gunn, D.E.3
Geraci, L.S.4
Jones, J.H.5
Sawicki, D.R.6
Sredy, J.7
Jacot, J.L.8
DiCioccio, A.T.9
Petrova, T.10
Mitschler, A.11
Podjarny, A.D.12
-
15
-
-
36148947863
-
-
f) M. Hranjec, M. Kralj, I. Piantanida, M. Sedic, L. Suman, K. Pavelic, G. Karminski-Zamola, J. Med. Chem. 2007, 50, 5696-5711;
-
(2007)
J. Med. Chem
, vol.50
, pp. 5696-5711
-
-
Hranjec, M.1
Kralj, M.2
Piantanida, I.3
Sedic, M.4
Suman, L.5
Pavelic, K.6
Karminski-Zamola, G.7
-
16
-
-
34548128318
-
-
g) M. L. Morningstar, T. Roth, D. W. Farnsworth, M. Kroeger Smith, K. Watson, R. W. Buckheit, Jr., K. Das, W. Zhang, E. Arnold, J. G. Julias, S. H. Hughes, C. J. Michejda, J. Med. Chem. 2007, 50, 4003-4015.
-
(2007)
J. Med. Chem
, vol.50
, pp. 4003-4015
-
-
Morningstar, M.L.1
Roth, T.2
Farnsworth, D.W.3
Kroeger Smith, M.4
Watson, K.5
Buckheit Jr., R.W.6
Das, K.7
Zhang, W.8
Arnold, E.9
Julias, J.G.10
Hughes, S.H.11
Michejda, C.J.12
-
17
-
-
33144476158
-
-
D. C. Tully, H. Liu, P. B. Alper, A. K. Chatterjee, R. Epple, M. J. Roberts, J. A. Williams, K. T. Nguyen, D. H. Woodmansee, C. Tumanut, J. Li, G. Spraggon, J. Chang, T. Tuntland, J. L. Harris, D. S. Karanewsky, Bioorg. Med. Chem. Lett. 2006, 16, 1975-1980.
-
(2006)
Bioorg. Med. Chem. Lett
, vol.16
, pp. 1975-1980
-
-
Tully, D.C.1
Liu, H.2
Alper, P.B.3
Chatterjee, A.K.4
Epple, R.5
Roberts, M.J.6
Williams, J.A.7
Nguyen, K.T.8
Woodmansee, D.H.9
Tumanut, C.10
Li, J.11
Spraggon, G.12
Chang, J.13
Tuntland, T.14
Harris, J.L.15
Karanewsky, D.S.16
-
18
-
-
34247202070
-
-
J. A. Grobler, G. Dornadula, M. R. Rice, A. L. Simcoe, D. J. Hazuda, M. D. Miller, J. Biol. Chem. 2007, 282, 8005-8010.
-
(2007)
J. Biol. Chem
, vol.282
, pp. 8005-8010
-
-
Grobler, J.A.1
Dornadula, G.2
Rice, M.R.3
Simcoe, A.L.4
Hazuda, D.J.5
Miller, M.D.6
-
19
-
-
33750120498
-
-
J. Easmon, G. Pürstinger, K.-S. Thies, G. Heinisch, J. Hofmann, J. Med. Chem. 2006, 49, 6343-6350.
-
(2006)
J. Med. Chem
, vol.49
, pp. 6343-6350
-
-
Easmon, J.1
Pürstinger, G.2
Thies, K.-S.3
Heinisch, G.4
Hofmann, J.5
-
20
-
-
33947194827
-
-
K. Rasmussen, M.-A. Hsu, Y. Yang, Neuropsychopharmacology 2007, 32, 786-792.
-
(2007)
Neuropsychopharmacology
, vol.32
, pp. 786-792
-
-
Rasmussen, K.1
Hsu, M.-A.2
Yang, Y.3
-
21
-
-
43449101554
-
-
a) R. D. Viirre, G. Evindar, R. A. Batey, J. Org. Chem. 2008, 73, 3452-3459;
-
(2008)
J. Org. Chem
, vol.73
, pp. 3452-3459
-
-
Viirre, R.D.1
Evindar, G.2
Batey, R.A.3
-
25
-
-
0037016981
-
-
J. Chang, K. Zhao, S. Pan, Tetrahedron Lett. 2002, 43, 951-954.
-
(2002)
Tetrahedron Lett
, vol.43
, pp. 951-954
-
-
Chang, J.1
Zhao, K.2
Pan, S.3
-
26
-
-
0030936878
-
-
R. S. Varma, R. K. Saini, O. Prakash, Tetrahedron Lett. 1997, 38, 2621-2622.
-
(1997)
Tetrahedron Lett
, vol.38
, pp. 2621-2622
-
-
Varma, R.S.1
Saini, R.K.2
Prakash, O.3
-
27
-
-
0030566822
-
-
K. H. Park, K. Jun, S. R. Shin, S. W. Oh, Tetrahedron Lett. 1996, 37, 8869-8870.
-
(1996)
Tetrahedron Lett
, vol.37
, pp. 8869-8870
-
-
Park, K.H.1
Jun, K.2
Shin, S.R.3
Oh, S.W.4
-
28
-
-
38649116932
-
-
C. Praveen, K. H. Kumar, D. Muralidharan, P. T. Perumal, Tetrahedron 2008, 64, 2369-2374.
-
(2008)
Tetrahedron
, vol.64
, pp. 2369-2374
-
-
Praveen, C.1
Kumar, K.H.2
Muralidharan, D.3
Perumal, P.T.4
-
30
-
-
0142106411
-
-
Y. Kawashita, N. Nakamichi, H. Kawabata, M. Hayashi, Org. Lett. 2003, 5, 3713-3715.
-
(2003)
Org. Lett
, vol.5
, pp. 3713-3715
-
-
Kawashita, Y.1
Nakamichi, N.2
Kawabata, H.3
Hayashi, M.4
-
31
-
-
33749525816
-
-
M. Kidwai, V. Bansal, A Saxena, S. Aerryb, S. Mozumdar, Tetrahedron Lett. 2006, 47, 8049-8053.
-
(2006)
Tetrahedron Lett
, vol.47
, pp. 8049-8053
-
-
Kidwai, M.1
Bansal, V.2
Saxena, A.3
Aerryb, S.4
Mozumdar, S.5
-
32
-
-
25444497767
-
-
a) B. Han, Q. Liu, Z.-G. Liu, R.-Z. Mu, W. Zhang, Z.-L. Liu, W. Yu, Synlett 2005, 2333-2334;
-
(2005)
Synlett
, pp. 2333-2334
-
-
Han, B.1
Liu, Q.2
Liu, Z.-G.3
Mu, R.-Z.4
Zhang, W.5
Liu, Z.-L.6
Yu, W.7
-
33
-
-
32644446862
-
-
b) B. Han, Z.-G. Liu, Q. Liu, L. Yang, Z.-L. Liu, W. Yu, Tetrahedron 2006, 62, 2492-2496.
-
(2006)
Tetrahedron
, vol.62
, pp. 2492-2496
-
-
Han, B.1
Liu, Z.-G.2
Liu, Q.3
Yang, L.4
Liu, Z.-L.5
Yu, W.6
-
34
-
-
53849089293
-
-
a) X. Wang, R. Liu, Y. Jin, X. Liang, Chem. Eur. J. 2008, 14, 2679-2685;
-
(2008)
Chem. Eur. J
, vol.14
, pp. 2679-2685
-
-
Wang, X.1
Liu, R.2
Jin, Y.3
Liang, X.4
-
35
-
-
1842502930
-
-
b) R. Liu, X. Liang, C. Dong, X. Hu, J. Am. Chem. Soc. 2004, 126, 4112-4113.
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 4112-4113
-
-
Liu, R.1
Liang, X.2
Dong, C.3
Hu, X.4
-
36
-
-
0037120130
-
-
It is well known that two kinds of resonance structures for TEMPO exist (I and II). The structures result from the unpaired electron delocalized between the nitrogen and the oxygen atoms. The greater the solvent polarity, the more favored structure II will be, as it has the larger electron density on the oxygen atom and spin density on the nitrogen atom. Structure II should reduce the hydrogen abstraction reactivity of TEMPO with phenols. Otherwise, the hydrogen-bonding interaction of TEMPO with protic solvents should disturb the interaction between TEMPO and phenols. See: a) P. Franchi, M. Marco Lucarini, P. Pedrielli, G. F. Pedulli, ChemPhysChem 2002, 3, 789-793, and references therein;
-
It is well known that two kinds of resonance structures for TEMPO exist (I and II). The structures result from the unpaired electron delocalized between the nitrogen and the oxygen atoms. The greater the solvent polarity, the more favored structure II will be, as it has the larger electron density on the oxygen atom and spin density on the nitrogen atom. Structure II should reduce the hydrogen abstraction reactivity of TEMPO with phenols. Otherwise, the hydrogen-bonding interaction of TEMPO with protic solvents should disturb the interaction between TEMPO and phenols. See: a) P. Franchi, M. Marco Lucarini, P. Pedrielli, G. F. Pedulli, ChemPhysChem 2002, 3, 789-793, and references therein;
-
-
-
-
37
-
-
0033532940
-
-
Chem. Soc, Chemical Equation Presented
-
b) L. R. C. Barclay, C. E. Edwards, M. R. Vinqvist, J. Am. Chem. Soc. 1999, 121, 6226-6231. (Chemical Equation Presented)
-
(1999)
J. Am
, vol.121
, pp. 6226-6231
-
-
Barclay, L.R.C.1
Edwards, C.E.2
Vinqvist, M.R.3
-
38
-
-
0003627253
-
-
The intermolecular hydrogen-bonding interaction between TEMPO and phenol has been studied both in solution and solid state. For solution studies, see: a I. G. Shenderovich, Z. Kecki, I. Wawer, G. S. Denisov, Spectrosc. Lett. 1997, 30, 1515-1523;
-
The intermolecular hydrogen-bonding interaction between TEMPO and phenol has been studied both in solution and solid state. For solution studies, see: a) I. G. Shenderovich, Z. Kecki, I. Wawer, G. S. Denisov, Spectrosc. Lett. 1997, 30, 1515-1523;
-
-
-
-
39
-
-
0035913772
-
-
for solid-state studies the single crystal structure of TEMPO·phenol adduct was obtained, see: b B. Ahrens, M. G. Davidson, V. T. Forsyth, M. F. Mahon, A. L. Johnson, S. A. Mason, R. D. Price, P. R. Raithby, J. Am. Chem. Soc. 2001, 123, 9164-9165.
-
for solid-state studies the single crystal structure of TEMPO·phenol adduct was obtained, see: b) B. Ahrens, M. G. Davidson, V. T. Forsyth, M. F. Mahon, A. L. Johnson, S. A. Mason, R. D. Price, P. R. Raithby, J. Am. Chem. Soc. 2001, 123, 9164-9165.
-
-
-
-
40
-
-
0344944928
-
-
For the hydrogen absraction between TEMPO and phenols, see: a
-
For the hydrogen absraction between TEMPO and phenols, see: a) C. Aliaga, A. Aspée, J. C. Scaiano, Org. Lett. 2003, 5, 4145-4148;
-
(2003)
Org. Lett
, vol.5
, pp. 4145-4148
-
-
Aliaga, C.1
Aspée, A.2
Scaiano, J.C.3
-
41
-
-
52649099049
-
-
b) C. Aliaga, J. M. Jua'rez-Ruiz, J. C. Scaiano, A. Aspée, Org. Lett. 2008, 10, 2147-2150.
-
(2008)
Org. Lett
, vol.10
, pp. 2147-2150
-
-
Aliaga, C.1
Jua'rez-Ruiz, J.M.2
Scaiano, J.C.3
Aspée, A.4
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