-
1
-
-
84956614279
-
-
Patai, S, Rappoport, Z, Eds, John Wiley & Sons: Chichester
-
(a) The Chemistry of the Quinonoid Compounds, Part 1 and 2, Vol. 2; Patai, S.; Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1988.
-
(1988)
The Chemistry of the Quinonoid Compounds, Part 1 and 2
, vol.2
-
-
-
2
-
-
0003868021
-
-
Thomson, R. H, Ed, Blackie Academic and Professional: London
-
(b) Naturally Occurring Quinones IV, Recent Advances; Thomson, R. H., Ed.; Blackie Academic and Professional: London, 1997.
-
(1997)
Naturally Occurring Quinones IV, Recent Advances
-
-
-
3
-
-
0002474992
-
-
Tamura, Y.; Yakura, T.; Tohma, H.; Kikuchi, K.; Kita, Y. Synthesis 1989, 126.
-
(1989)
Synthesis
, pp. 126
-
-
Tamura, Y.1
Yakura, T.2
Tohma, H.3
Kikuchi, K.4
Kita, Y.5
-
6
-
-
0026507192
-
-
(c) Claudio, S. B.; Valderrama, J. A.; Tapia, R.; Farina, F.; Paredes, M. C. Synth. Commun. 1992, 22, 955.
-
(1992)
Synth. Commun
, vol.22
, pp. 955
-
-
Claudio, S.B.1
Valderrama, J.A.2
Tapia, R.3
Farina, F.4
Paredes, M.C.5
-
8
-
-
0035944184
-
-
Tohma, H.; Morioka, H.; Harayama, Y.; Hashizume, M.; Kita, Y. Tetrahedron Lett. 2001, 42, 6899.
-
(2001)
Tetrahedron Lett
, vol.42
, pp. 6899
-
-
Tohma, H.1
Morioka, H.2
Harayama, Y.3
Hashizume, M.4
Kita, Y.5
-
9
-
-
0001213492
-
-
For recent reviews, see: a
-
For recent reviews, see: (a) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
-
(1996)
Chem. Rev
, vol.96
, pp. 1123
-
-
Stang, P.J.1
Zhdankin, V.V.2
-
10
-
-
0001382837
-
-
(b) Kita, Y.; Takada, T.; Tohma, H. Pure Appl. Chem. 1996, 68, 627.
-
(1996)
Pure Appl. Chem
, vol.68
, pp. 627
-
-
Kita, Y.1
Takada, T.2
Tohma, H.3
-
12
-
-
0003579937
-
-
Varvoglis, A, Ed, Academic Press: San Diego
-
(d) Hypervalent Iodine in Organic Synthesis; Varvoglis, A., Ed.; Academic Press: San Diego, 1997.
-
(1997)
Hypervalent Iodine in Organic Synthesis
-
-
-
15
-
-
0001392451
-
-
(g) Muraki, T.; Togo, H.; Yokoyama, M. Rev. Heteroatom Chem. 1997, 17, 213.
-
(1997)
Rev. Heteroatom Chem
, vol.17
, pp. 213
-
-
Muraki, T.1
Togo, H.2
Yokoyama, M.3
-
18
-
-
0035800351
-
-
For reviews, see: a
-
For reviews, see: (a) Wirth, T. Angew. Chem. Int. Ed. 2001, 40, 2812.
-
(2001)
Angew. Chem. Int. Ed
, vol.40
, pp. 2812
-
-
Wirth, T.1
-
23
-
-
0032745171
-
-
(b) Togo, H.; Abe, S.; Nogami, G.; Yokoyama, M. Bull. Chem. Soc. Jpn. 1999, 72, 2351.
-
(1999)
Bull. Chem. Soc. Jpn
, vol.72
, pp. 2351
-
-
Togo, H.1
Abe, S.2
Nogami, G.3
Yokoyama, M.4
-
24
-
-
0001645943
-
-
(c) Ley, S. V.; Thomas, A. W.; Finch, H. J. Chem. Soc., Perkin Trans. 1 1999, 669.
-
(1999)
J. Chem. Soc., Perkin Trans. 1
, pp. 669
-
-
Ley, S.V.1
Thomas, A.W.2
Finch, H.3
-
25
-
-
33746467034
-
-
(d) Ley, S. V.; Schucht, O.; Thomas, A. W.; Murray, P. J. J. Chem. Soc., Perkin Trans. 1 1999, 1251.
-
(1999)
J. Chem. Soc., Perkin Trans. 1
, pp. 1251
-
-
Ley, S.V.1
Schucht, O.2
Thomas, A.W.3
Murray, P.J.4
-
26
-
-
0034599884
-
-
(e) Tohma, H.; Takizawa, S.; Maegawa, T.; Kita, Y. Angew. Chem. Int. Ed. 2000, 39, 1306.
-
(2000)
Angew. Chem. Int. Ed
, vol.39
, pp. 1306
-
-
Tohma, H.1
Takizawa, S.2
Maegawa, T.3
Kita, Y.4
-
27
-
-
0003571474
-
-
(f) Tohma, H.; Maegawa, T.; Takizawa, S.; Kita, Y. Adv. Synth. Catal. 2002, 328.
-
(2002)
Adv. Synth. Catal
, pp. 328
-
-
Tohma, H.1
Maegawa, T.2
Takizawa, S.3
Kita, Y.4
-
30
-
-
25844524611
-
-
Dohi, T.; Maruyama, A.; Yoshimura, M.; Morimoto, K.; Tohma, H.; Kita, Y. Angew. Chem. Int. Ed. 2005, 44, 6193.
-
(2005)
Angew. Chem. Int. Ed
, vol.44
, pp. 6193
-
-
Dohi, T.1
Maruyama, A.2
Yoshimura, M.3
Morimoto, K.4
Tohma, H.5
Kita, Y.6
-
31
-
-
24644495096
-
-
Ochiai, M.; Takeuchi, Y.; Katayama, T.; Sueda, T.; Miyamoto, K. J. Am. Chem. Soc. 2005, 127, 12244.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 12244
-
-
Ochiai, M.1
Takeuchi, Y.2
Katayama, T.3
Sueda, T.4
Miyamoto, K.5
-
33
-
-
22244435262
-
-
Thottumkara, A. P.; Bowsher, M. S.; Vinod, T. K. Org. Lett. 2005, 7, 2933.
-
(2005)
Org. Lett
, vol.7
, pp. 2933
-
-
Thottumkara, A.P.1
Bowsher, M.S.2
Vinod, T.K.3
-
35
-
-
0021206946
-
-
Compound 1a is commercially available. For preparation, see: Abraham, D. J.; Kennedy, P. E.; Mehanna, A. S.; Patwa, D. C.; Williums, F. L. J. Med. Chem. 1984, 27, 967.
-
Compound 1a is commercially available. For preparation, see: Abraham, D. J.; Kennedy, P. E.; Mehanna, A. S.; Patwa, D. C.; Williums, F. L. J. Med. Chem. 1984, 27, 967.
-
-
-
-
36
-
-
33746231801
-
-
Marcotullio, M. C.; Epifano, F.; Curini, M. Trends Org. Chem. 2003, 10, 21.
-
(2003)
Trends Org. Chem
, vol.10
, pp. 21
-
-
Marcotullio, M.C.1
Epifano, F.2
Curini, M.3
-
37
-
-
33746211332
-
-
3 has been reported, see: Carreño, M. C.; González-López, M.; Urbano, A. Angew. Chem. Int. Ed. 2006, 45, 2737.
-
3 has been reported, see: Carreño, M. C.; González-López, M.; Urbano, A. Angew. Chem. Int. Ed. 2006, 45, 2737.
-
-
-
-
38
-
-
3342981841
-
-
It is not clear whether iodine(V) species was formed during the reaction. However, many reports for the formation of iodine(V) species by the oxidation of iodoarene with oxidizing reagent have been reported, see: (a) Kennedy, R. J.; Stock, A. M. J. Org. Chem. 1960, 25, 1901.
-
It is not clear whether iodine(V) species was formed during the reaction. However, many reports for the formation of iodine(V) species by the oxidation of iodoarene with oxidizing reagent have been reported, see: (a) Kennedy, R. J.; Stock, A. M. J. Org. Chem. 1960, 25, 1901.
-
-
-
-
40
-
-
37049096772
-
-
(c) Barton, D. H. R.; Godfrey, C. R. A.; Morzycki, J. W.; Motherwell, W. B.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1982, 1947.
-
(1982)
J. Chem. Soc., Perkin Trans. 1
, pp. 1947
-
-
Barton, D.H.R.1
Godfrey, C.R.A.2
Morzycki, J.W.3
Motherwell, W.B.4
Ley, S.V.5
-
41
-
-
0011668108
-
-
(d) Kazmierczak, P.; Skulski, L.; Kraszkiewicz, L. Molecules 2001, 6, 881.
-
(2001)
Molecules
, vol.6
, pp. 881
-
-
Kazmierczak, P.1
Skulski, L.2
Kraszkiewicz, L.3
-
45
-
-
33750492632
-
-
(h) Koposov, A. Y.; Karimov, R. R.; Geraskin, I. M.; Nemykin, V. N.; Zhdankin, V. V. J. Org. Chem. 2006, 71, 8452.
-
(2006)
J. Org. Chem
, vol.71
, pp. 8452
-
-
Koposov, A.Y.1
Karimov, R.R.2
Geraskin, I.M.3
Nemykin, V.N.4
Zhdankin, V.V.5
-
46
-
-
33845960262
-
-
(i) Koposov, A. Y.; Karimov, R. R.; Pronin, A. A.; Skrupskaya, T.; Yusubov, M. S.; Zhdankin, V. V. J. Org. Chem. 2006, 71, 9912.
-
(2006)
J. Org. Chem
, vol.71
, pp. 9912
-
-
Koposov, A.Y.1
Karimov, R.R.2
Pronin, A.A.3
Skrupskaya, T.4
Yusubov, M.S.5
Zhdankin, V.V.6
-
47
-
-
0000978251
-
-
For the oxidation of phenol derivatives with iodine(V) species, see ref. 3b and: Barton, D. H. R.; Godfrey, C. R. A.; Morzycki, J. W.; Motherwell, W. B.; Stobie, A. Tetrahedron Lett. 1982, 23, 957.
-
For the oxidation of phenol derivatives with iodine(V) species, see ref. 3b and: Barton, D. H. R.; Godfrey, C. R. A.; Morzycki, J. W.; Motherwell, W. B.; Stobie, A. Tetrahedron Lett. 1982, 23, 957.
-
-
-
-
48
-
-
33947724035
-
-
It is possible that iodine(III) species may be oxidized by Oxone® to regenerate iodine(V) species before the reaction of iodine(III) with phenol
-
It is possible that iodine(III) species may be oxidized by Oxone® to regenerate iodine(V) species before the reaction of iodine(III) with phenol.
-
-
-
-
49
-
-
33947714789
-
-
Typical Reaction Procedure: To a solution of 2 (1 mmol) in MeCN-H2O (2:1, 6 mL) was added 1a (0.2 mmol) followed by Oxone® (1 mmol) at r.t. and the resulting mixture was stirred at the same temperature. After 2 was completely consumed indicated by TLC, the mixture was diluted with EtOAc and washed with H2O. The organic layer was then washed with aq sat. NaHCO3 solution and dried, concentrated to give pure 3. If necessary, the product was purified by column chromatography on silica gel to give pure quinone. The alkaline solution was acidified by 10% HCl solution and extracted with EtOAc. The organic layer was washed with aq Na2S2O3 solution and dried, then concentrated to give recovered 1a which was purified by recrystallization from Et2O-hexane. All new compounds gave satisfactory spectroscopic data
-
2O-hexane. All new compounds gave satisfactory spectroscopic data.
-
-
-
|