-
1
-
-
56249137056
-
-
For the synthesis of IBX, see: (a) Hartmann, C.; Meyer, V. Chem. Ber. 1893, 26, 1727-1732.
-
(1893)
Chem. Ber.
, vol.26
, pp. 1727-1732
-
-
Hartmann, C.1
Meyer, V.2
-
2
-
-
0033546262
-
-
(b) Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 4537-4538
-
-
Frigerio, M.1
Santagostino, M.2
Sputore, S.3
-
4
-
-
0000565339
-
-
(b) De Munari, S.; Frigerio, M.; Santagostino, M. J. Org. Chem. 1996, 61, 9272-9279.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 9272-9279
-
-
De Munari, S.1
Frigerio, M.2
Santagostino, M.3
-
6
-
-
22244435262
-
-
(d) Thottumkara, A. P.; Bowsher, M. S.; Vinod, T. K. Org. Lett. 2005, 7, 2933-2936.
-
(2005)
Org. Lett.
, vol.7
, pp. 2933-2936
-
-
Thottumkara, A.P.1
Bowsher, M.S.2
Vinod, T.K.3
-
9
-
-
20544472300
-
-
(c) Kumar, I. Synlett 2005, 1488-1489.
-
(2005)
Synlett
, pp. 1488-1489
-
-
Kumar, I.1
-
11
-
-
0034602983
-
-
(a) Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 625-628.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 625-628
-
-
Nicolaou, K.C.1
Zhong, Y.-L.2
Baran, P.S.3
-
12
-
-
0034679468
-
-
(b) Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 2525-2529.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 2525-2529
-
-
Nicolaou, K.C.1
Zhong, Y.-L.2
Baran, P.S.3
-
13
-
-
0034829609
-
-
(c) Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. J. Am. Chem. Soc. 2001, 123, 3183-3185.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 3183-3185
-
-
Nicolaou, K.C.1
Zhong, Y.-L.2
Baran, P.S.3
-
14
-
-
1942536050
-
-
(d) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192-5201.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 5192-5201
-
-
Nicolaou, K.C.1
Mathison, C.J.N.2
Montagnon, T.3
-
16
-
-
0034625897
-
-
(a) Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. J. Am. Chem. Soc. 2000, 122, 7596-7597.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 7596-7597
-
-
Nicolaou, K.C.1
Zhong, Y.-L.2
Baran, P.S.3
-
17
-
-
0037070535
-
-
(b) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245-2258.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 2245-2258
-
-
Nicolaou, K.C.1
Montagnon, T.2
Baran, P.S.3
Zhong, Y.-L.4
-
18
-
-
0037087704
-
-
(c) Nicolaou, K. C.; Montagnon, T.; Baran, P. S. Angew. Chem., Int. Ed. 2002, 41, 993-996.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 993-996
-
-
Nicolaou, K.C.1
Montagnon, T.2
Baran, P.S.3
-
19
-
-
0037087571
-
-
(d) Nicolaou, K. C.; Gray, D. L. F.; Montagnon, T.; Harrison, S. T. Angew. Chem., Int. Ed. 2002, 41, 996-1000.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 996-1000
-
-
Nicolaou, K.C.1
Gray, D.L.F.2
Montagnon, T.3
Harrison, S.T.4
-
20
-
-
28044467170
-
-
note
-
Besides the more likely SET-based mechanism, an ionic mechanism was discussed for the IBX-mediated dehydrogenation of carbonyl compounds: ref 5b.
-
-
-
-
21
-
-
28044457231
-
-
note
-
The reaction of p-cresol with IBX gave 4-methyl-1,2-bisphenol: ref 5b.
-
-
-
-
22
-
-
28044442979
-
-
note
-
The benzylic oxidation using IBX can be explained via intramolecular oxygen transfer: ref 5b.
-
-
-
-
23
-
-
0037165401
-
-
(a) Magdziak, D.; Rodriguez, A. A.; Van De Water, R. W.; Pettus, T. R. R. Org. Lett. 2002, 4, 285-288.
-
(2002)
Org. Lett.
, vol.4
, pp. 285-288
-
-
Magdziak, D.1
Rodriguez, A.A.2
Van De Water, R.W.3
Pettus, T.R.R.4
-
24
-
-
9444236739
-
-
(b) Shibuya, M.; Ito, S.; Takahashi, M.; Iwabuchi, Y. Org. Lett. 2004, 6, 4303-4306.
-
(2004)
Org. Lett.
, vol.6
, pp. 4303-4306
-
-
Shibuya, M.1
Ito, S.2
Takahashi, M.3
Iwabuchi, Y.4
-
25
-
-
0000271393
-
-
Trost, B. M., Fleming, I., Eds.; Pergamon: New York
-
(a) Jones, A. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 7, pp 151-191.
-
(1991)
Comprehensive Organic Synthesis
, vol.7
, pp. 151-191
-
-
Jones, A.B.1
-
26
-
-
0009506491
-
-
Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: New York
-
(b) Davis, F. A.; Chen, B.-C. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: New York, 1995; Vol. E21b, pp 4497-4518.
-
(1995)
Methods of Organic Chemistry (Houben-Weyl), 4th Ed.
, vol.E21B
, pp. 4497-4518
-
-
Davis, F.A.1
Chen, B.-C.2
-
27
-
-
1842603677
-
-
(c) Chen, B.-C.; Zhou, P.; Davis, F. A.; Ciganek, E. Org. React. 2003, 62, 1-356.
-
(2003)
Org. React.
, vol.62
, pp. 1-356
-
-
Chen, B.-C.1
Zhou, P.2
Davis, F.A.3
Ciganek, E.4
-
28
-
-
0001743040
-
-
For selected examples for the synthesis of tertiary alcohols via α-hydroxylation of carbonyl compounds, see: (a) Davis, F. A.; Weismiller, M. C. J. Org. Chem. 1990, 55, 3715-3717.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 3715-3717
-
-
Davis, F.A.1
Weismiller, M.C.2
-
30
-
-
1942535162
-
-
Christoffers, J.; Baro, A.; Werner, T. Adv. Synth. Catal. 2004, 346, 143-151.
-
(2004)
Adv. Synth. Catal.
, vol.346
, pp. 143-151
-
-
Christoffers, J.1
Baro, A.2
Werner, T.3
-
31
-
-
28044472813
-
-
note
-
Other hypervalent iodine compounds were not used in such α-hydroxylations.
-
-
-
-
32
-
-
28044446597
-
-
note
-
Ketone 1 was detected as the intermediary occurring species in the transformation 4 → 2 by capillary gas chromatography and by thin-layer chromatography.
-
-
-
-
34
-
-
33845556989
-
-
(b) Murray, T. F.; Samsel, E. G.; Varma, V.; Norton, J. R. J. Am. Chem. Soc. 1981, 103, 7520-7528.
-
(1981)
J. Am. Chem. Soc.
, vol.103
, pp. 7520-7528
-
-
Murray, T.F.1
Samsel, E.G.2
Varma, V.3
Norton, J.R.4
-
35
-
-
28044455273
-
-
note
-
Adding IBX at once to the reaction mixture gave varying yields for the conversion 1a → 2b (51-88%).
-
-
-
-
36
-
-
28044450430
-
-
note
-
The origin of this effect remains unclear.
-
-
-
-
37
-
-
28044436546
-
-
note
-
A facile dehydration of the tertiary alcohols 2 giving α,β-unsaturated carbonyl compounds 3 was not observed under these conditions.
-
-
-
-
38
-
-
28044444133
-
-
note
-
Tertiary alcohols were not detected as intermediary species in the IBX-mediated dehydrogenation of carbonyl compounds.
-
-
-
|