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Naturally Occurring Quinones IV Recent Advances, ed. by Thomson R. H., Blackie Academic & Professional, London, 1997.
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"Naturally Occurring Quinones IV Recent Advances," ed. by Thomson R. H., Blackie Academic & Professional, London, 1997.
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3
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Hypervalent Iodine in Organic Synthesis, ed. by Varvoglis A., Academic Press, San Diego, 1997.
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"Hypervalent Iodine in Organic Synthesis," ed. by Varvoglis A., Academic Press, San Diego, 1997.
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31
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55749091573
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Typical reaction procedure: Compound 1 (0.050 mmol) was added to a solution of 2 (1.0 mmol) in CF3CH2OH-H 2O (1:2, 10 ml, followed by Oxone® (4 mmol) at room temperature, the resulting mixture was stirred at the same temperature. After 2 was consumed completely, as indicated by TLC, the mixture was diluted with ethyl acetate and washed with water. The organic layer was then washed with aqueous saturated sodium bicarbonate solution and dried, then concentrated to give pure 3. If necessary, the product was purified using column chromatography on silica gel to give pure quinone. The alkaline solution was acidified by 10% hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with aqueous sodium thiosulfate solution and dried, then concentrated to recover 1 75-85, which was purified by recrystallization from diethyl ether-hexane. All new compounds gave satisfactory spectrospecific
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2O (1:2, 10 ml), followed by Oxone® (4 mmol) at room temperature, the resulting mixture was stirred at the same temperature. After 2 was consumed completely, as indicated by TLC, the mixture was diluted with ethyl acetate and washed with water. The organic layer was then washed with aqueous saturated sodium bicarbonate solution and dried, then concentrated to give pure 3. If necessary, the product was purified using column chromatography on silica gel to give pure quinone. The alkaline solution was acidified by 10% hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with aqueous sodium thiosulfate solution and dried, then concentrated to recover 1 (75-85%) which was purified by recrystallization from diethyl ether-hexane. All new compounds gave satisfactory spectrospecific data.
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32
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55749096728
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2O showed no presence of hypervalent iodine species.
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2O showed no presence of hypervalent iodine species.
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33
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55749089526
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Many reports for the formation of hypervalent iodine species by the oxidation of iodoarene with Oxone® have appeared.36-41
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36-41)
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34
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55749098770
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4: 222.08921).
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4: 222.08921).
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35
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55749092110
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Although Nojima et al. reported oxidation of 8 with CAN, that report includes no description related to detailed reaction conditions and yield.7
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7)
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36
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0033546262
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Frigerio M., Santagostino M., Sputore S., J. Org. Chem., 64, 4537-4538 (1999).
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30944435292
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Ladziata, U.1
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Zhdankin, V.V.3
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33750851168
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Koposov A. Y., Litvinov D. N., Zhdankin V. V., Ferguson M. J., McDonald R., Tykwinski R. R., Eur. J. Org. Chem., 2006, 4791-4795 (2006).
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Litvinov, D.N.2
Zhdankin, V.V.3
Ferguson, M.J.4
McDonald, R.5
Tykwinski, R.R.6
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41
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35348923492
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Karimov R. R., Kazhkenov Z.-G. M., Modjewski M. J., Peterson E. M., Zhdankin V. V., J. Org. Chem., 72, 8149-8151 (2007).
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Karimov, R.R.1
Kazhkenov, Z.-G.M.2
Modjewski, M.J.3
Peterson, E.M.4
Zhdankin, V.V.5
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