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1
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0003641908
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Kadish, K. M, Smith, K. M, Guilard, R, Eds, Academic Press: San Diego, Vols
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The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 1999-2003; Vols. 1-20.
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(1999)
The Porphyrin Handbook
, vol.1-20
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2
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0036979998
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We have developed porphyrin-based Lewis acid catalysts that can promote regio- and stereoselective isomerization of epoxides to carbonyl compounds and Claisen rearrangement of allylvinyl ethers; see: (a) Suda, K, Baba, K, Nakajima, S, Takanami, T. Chem. Commun. 2002, 2570-2571
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We have developed porphyrin-based Lewis acid catalysts that can promote regio- and stereoselective isomerization of epoxides to carbonyl compounds and Claisen rearrangement of allylvinyl ethers; see: (a) Suda, K.; Baba, K.; Nakajima, S.; Takanami, T. Chem. Commun. 2002, 2570-2571.
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3
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3543079935
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(b) Suda, K.; Kikkawa, T.; Nakajima, S.; Takanami, T. J. Am. Chem. Soc. 2004, 126, 9554-9555.
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(2004)
J. Am. Chem. Soc
, vol.126
, pp. 9554-9555
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Suda, K.1
Kikkawa, T.2
Nakajima, S.3
Takanami, T.4
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4
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15944416400
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(c) Takanami, T.; Hayashi, M.; Suda, K. Tetrahedron Lett. 2005, 46, 2893-2896.
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(2005)
Tetrahedron Lett
, vol.46
, pp. 2893-2896
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Takanami, T.1
Hayashi, M.2
Suda, K.3
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5
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33747810388
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(d) Takanami, T.; Hayashi, M.; Iso, K.; Nakamoto, H.; Suda, K. Tetrahedron 2006, 62, 9467-9474.
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(2006)
Tetrahedron
, vol.62
, pp. 9467-9474
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Takanami, T.1
Hayashi, M.2
Iso, K.3
Nakamoto, H.4
Suda, K.5
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6
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85006518549
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For some examples of leading works on functionalization reactions of porphyrins, see: a
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For some examples of leading works on functionalization reactions of porphyrins, see: (a) DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513-2515.
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(1993)
J. Am. Chem. Soc
, vol.115
, pp. 2513-2515
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DiMagno, S.G.1
Lin, V.S.-Y.2
Therien, M.J.3
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7
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0028903953
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(b) Boyle, R. W.; Johnson, C. K.; Dolphin, D. J. Chem. Soc., Chem. Commun. 1995, 527-528.
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(1995)
J. Chem. Soc., Chem. Commun
, pp. 527-528
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Boyle, R.W.1
Johnson, C.K.2
Dolphin, D.3
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8
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34249104602
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(c) Yamaguchi, S.; Katoh, T.; Shinkubo, H.; Osuka, A. J. Am. Chem. Soc. 2007, 129, 6392-6393.
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(2007)
J. Am. Chem. Soc
, vol.129
, pp. 6392-6393
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Yamaguchi, S.1
Katoh, T.2
Shinkubo, H.3
Osuka, A.4
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9
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34247338978
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(d) Liu, C.; Shen, D.-M.; Chen, Q.-Y. J. Org. Chem. 2007, 72, 2732-2736.
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(2007)
J. Org. Chem
, vol.72
, pp. 2732-2736
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Liu, C.1
Shen, D.-M.2
Chen, Q.-Y.3
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10
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26644434833
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have developed a unique, yet useful, method for the preparation of meso-substituted porphyrins utilizing an SNAr reaction with organolithium reagents: (a) Senge, M. O
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Senge et al. have developed a unique, yet useful, method for the preparation of meso-substituted porphyrins utilizing an SNAr reaction with organolithium reagents: (a) Senge, M. O. Acc. Chem. Res. 2005, 38, 733-743.
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(2005)
Acc. Chem. Res
, vol.38
, pp. 733-743
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Senge1
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11
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6444234869
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(b) Senge, M. O.; Hatscher, S. S.; Wiehe, A.; Dahns, K.; Kelling, A. J. Am. Chem. Soc. 2004, 126, 13634-13635.
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(2004)
J. Am. Chem. Soc
, vol.126
, pp. 13634-13635
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Senge, M.O.1
Hatscher, S.S.2
Wiehe, A.3
Dahns, K.4
Kelling, A.5
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13
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0042381716
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We have reported metal-catalyzed amination and cyanation of porphyrins: (a) Takanami, T, Hayashi, M, Hino, F, Suda, K. Tetrahedron Lett. 2003, 44, 7353-7357
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We have reported metal-catalyzed amination and cyanation of porphyrins: (a) Takanami, T.; Hayashi, M.; Hino, F.; Suda, K. Tetrahedron Lett. 2003, 44, 7353-7357.
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14
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24944506824
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(b) Takanami, T.; Hayashi, M.; Chijimatsu, H.; Inoue, W.; Suda, K. Org. Lett. 2005, 7, 3937-3940.
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(2005)
Org. Lett
, vol.7
, pp. 3937-3940
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Takanami, T.1
Hayashi, M.2
Chijimatsu, H.3
Inoue, W.4
Suda, K.5
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15
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3543014369
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For reviews, see: a
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For reviews, see: (a) Balakumar, A.; Muthukumaran, K.; Lindsey, J. S. J. Org. Chem. 2004, 69, 5112-5115.
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(2004)
J. Org. Chem
, vol.69
, pp. 5112-5115
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Balakumar, A.1
Muthukumaran, K.2
Lindsey, J.S.3
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18
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84982072747
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(b) Inhoffen, H. H.; Fuhrhop, J.-H.; Voigt, H.; Brockmann, H., Jr. Justus Liebigs Ann. Chem. 1966, 695, 133-143.
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(1966)
Justus Liebigs Ann. Chem
, vol.695
, pp. 133-143
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Inhoffen, H.H.1
Fuhrhop, J.-H.2
Voigt, H.3
Brockmann Jr., H.4
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19
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37049108535
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(c) Smith, K. M.; Bisset, G. M. F.; Tabba, H. D. J. Chem. Soc., Perkin. Trans. 1 1982, 581-585.
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(1982)
J. Chem. Soc., Perkin. Trans. 1
, pp. 581-585
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Smith, K.M.1
Bisset, G.M.F.2
Tabba, H.D.3
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20
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0033117436
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and references cited therein
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(d) Ando, A.; Yamazaki, M.; Komura, M.; Sano, Y.; Hattori, N.; Omote, M.; Kumadaki, I. Heterocycles 1999, 50, 913-918 and references cited therein.
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(1999)
Heterocycles
, vol.50
, pp. 913-918
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Ando, A.1
Yamazaki, M.2
Komura, M.3
Sano, Y.4
Hattori, N.5
Omote, M.6
Kumadaki, I.7
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21
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39749146293
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A multi-step total synthesis of free base meso-formylporphyrins has been reported by Lindsey et al, see ref 6a
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A multi-step total synthesis of free base meso-formylporphyrins has been reported by Lindsey et al.; see ref 6a.
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22
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0001122697
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For reviews: a, Trost, B. M, Fleming, I, Eds, Pergamon: Oxford
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For reviews: (a) Colvin, E. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 7, pp 641-651.
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(1991)
Comprehensive Organic Synthesis
, vol.7
, pp. 641-651
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Colvin, E.W.1
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24
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0033166413
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(a) Itami, K.; Mitsudo, K.; Yoshida, J. Tetrahedron Lett. 1999, 40, 5533-5536.
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(1999)
Tetrahedron Lett
, vol.40
, pp. 5533-5536
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Itami, K.1
Mitsudo, K.2
Yoshida, J.3
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25
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0033165956
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(b) Itami, K.; Mitsudo, K.; Yoshida, J. Tetrahedron Lett. 1999, 40, 5537-5540.
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(1999)
Tetrahedron Lett
, vol.40
, pp. 5537-5540
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Itami, K.1
Mitsudo, K.2
Yoshida, J.3
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26
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0035356076
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(c) Itami, K.; Kamei, T.; Mitsudo, K.; Nokami, T.; Yoshida, J. J. Org. Chem. 2001, 66, 3970-3976.
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(2001)
J. Org. Chem
, vol.66
, pp. 3970-3976
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Itami, K.1
Kamei, T.2
Mitsudo, K.3
Nokami, T.4
Yoshida, J.5
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39749155617
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Although we have failed in isolating meso-hydroxymethylporphyrin 5a, a key synthetic intermediate in this formylation, TLC analysis snowed that the hydroxymethyl derivative 5a transiently appears during the course of the reaction: the Rf value (0.21, THF/hexane, 1:2) of the hydroxymethyl derivative 5a proved to be identical to that of an authentic sample independently prepared by the reduction of the meso-formylporphyrin 2a with NaBH4 in THF/MeOH (3:1) at room temperature
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4 in THF/MeOH (3:1) at room temperature.
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28
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39749130829
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Although details of the oxidation processes of silylmethylporphyrin 4 and hydroxymethylporphyrin 5 are not yet clear, we tentatively assume the mechanism depicted in the following scheme, where each oxidation reaction is initiated by a single-electron transfer from the respective compounds, 4 and 5 (see refs 13 and 14, to DDQ, a well-known electron acceptor see refs 15 and 16, Further experiments are currently underway to elucidate the mechanism in detail
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Although details of the oxidation processes of silylmethylporphyrin 4 and hydroxymethylporphyrin 5 are not yet clear, we tentatively assume the mechanism depicted in the following scheme, where each oxidation reaction is initiated by a single-electron transfer from the respective compounds, 4 and 5 (see refs 13 and 14), to DDQ, a well-known electron acceptor (see refs 15 and 16). Further experiments are currently underway to elucidate the mechanism in detail.
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33646462101
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For reviews on electron-transfer oxidation of organosilicon compounds, see: a
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For reviews on electron-transfer oxidation of organosilicon compounds, see: (a) Yoshida, J.; Nishiwaki, K. J. Chem. Soc., Dalton Trans 1998, 2589-2596.
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(1998)
J. Chem. Soc., Dalton Trans
, pp. 2589-2596
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Yoshida, J.1
Nishiwaki, K.2
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30
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0002582711
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Steckhan, E, Ed, Springer-Verlag: Berlin
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(b) Yoshida, J. In Electrochemistry V, Topics in Current Chemistry, Vol. 170; Steckhan, E., Ed.; Springer-Verlag: Berlin, 1994; pp 39-81.
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(1994)
Electrochemistry V, Topics in Current Chemistry
, vol.170
, pp. 39-81
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Yoshida, J.1
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31
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0003972955
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For reviews on electron-transfer oxidation of alcohols, see: a, Springer-Verlag: Berlin
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For reviews on electron-transfer oxidation of alcohols, see: (a) Shono, T. Electroorganic Chemistry as a New Tool in Organic Synthesis; Springer-Verlag: Berlin, 1984; pp 29-38.
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(1984)
Electroorganic Chemistry as a New Tool in Organic Synthesis
, pp. 29-38
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Shono, T.1
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33
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84957375796
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Patai, S, Ed, Wiley: New York
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Foster, R.; Foreman, M. L. In The Chemistry of the Quinonoid Compounds, Part 1; Patai, S., Ed.; Wiley: New York, 1974; pp 257-333.
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(1974)
The Chemistry of the Quinonoid Compounds, Part 1
, pp. 257-333
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Foster, R.1
Foreman, M.L.2
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34
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and references cited therein. Several groups have reported that DDQ can oxidize aryl methanols to aromatic aldehydes; see
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Several groups have reported that DDQ can oxidize aryl methanols to aromatic aldehydes; see: Branytska, O.; Neumann, R. Synlett 2004, 1575-1576 and references cited therein.
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(2004)
Synlett
, pp. 1575-1576
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Branytska, O.1
Neumann, R.2
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35
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39749193773
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2/MeOH (3:1) at room temperature gave the corresponding Zn(II) complexes in quantitative yields.
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2/MeOH (3:1) at room temperature gave the corresponding Zn(II) complexes in quantitative yields.
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