-
1
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84891568337
-
-
Bäckvall J.-E. (Ed), Wiley-VCH, Weinheim
-
In: Bäckvall J.-E. (Ed). Modern Oxidation Methods (2004), Wiley-VCH, Weinheim
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(2004)
Modern Oxidation Methods
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4
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38649142495
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See for example:
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See for example:
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7
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0000208820
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Zefirov N.S., Zhdankin V.V., Dan'kov Yu.V., Sorokin V.D., Semerikov V.N., Koz'min A.S., Caple R., and Berglund B.A. Tetrahedron Lett. (1986) 3971-3974
-
(1986)
Tetrahedron Lett.
, pp. 3971-3974
-
-
Zefirov, N.S.1
Zhdankin, V.V.2
Dan'kov, Yu.V.3
Sorokin, V.D.4
Semerikov, V.N.5
Koz'min, A.S.6
Caple, R.7
Berglund, B.A.8
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9
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33646083667
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-
Çelik M., Alp C., Coskun B., Gültekin M.S., and Balci M. Tetrahedron Lett. (2006) 3659-3663
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(2006)
Tetrahedron Lett.
, pp. 3659-3663
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-
Çelik, M.1
Alp, C.2
Coskun, B.3
Gültekin, M.S.4
Balci, M.5
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10
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38649094002
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For recent reviews on the synthetic applications of polyvalent iodine reagents, see:
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For recent reviews on the synthetic applications of polyvalent iodine reagents, see:
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19
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0037459842
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Serna S., Tellitu I., Domínguez E., Moreno I., and SanMartín R. Tetrahedron Lett. (2003) 3483-3486
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(2003)
Tetrahedron Lett.
, pp. 3483-3486
-
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Serna, S.1
Tellitu, I.2
Domínguez, E.3
Moreno, I.4
SanMartín, R.5
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20
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33846446683
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Tellitu I., Urrejola A., Serna S., Moreno I., Herrero M.T., Domínguez E., SanMartin R., and Correa A. Eur. J. Org. Chem. (2007) 437-444
-
(2007)
Eur. J. Org. Chem.
, pp. 437-444
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Tellitu, I.1
Urrejola, A.2
Serna, S.3
Moreno, I.4
Herrero, M.T.5
Domínguez, E.6
SanMartin, R.7
Correa, A.8
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23
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38649085679
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For some recent contributions from our group, see:
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For some recent contributions from our group, see:
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24
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0035908196
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Moreno I., Tellitu I., Etayo J., SanMartin R., and Domínguez E. Tetrahedron 57 (2001) 5403-5411
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(2001)
Tetrahedron
, vol.57
, pp. 5403-5411
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Moreno, I.1
Tellitu, I.2
Etayo, J.3
SanMartin, R.4
Domínguez, E.5
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25
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22244442449
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Serna S., Tellitu I., Domínguez E., Moreno I., and SanMartin R. Org. Lett. 7 (2005) 3073-3076
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(2005)
Org. Lett.
, vol.7
, pp. 3073-3076
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Serna, S.1
Tellitu, I.2
Domínguez, E.3
Moreno, I.4
SanMartin, R.5
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26
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15444370706
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Correa A., Tellitu I., Domínguez E., Moreno I., and SanMartin R. J. Org. Chem. 70 (2005) 2256-2264
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(2005)
J. Org. Chem.
, vol.70
, pp. 2256-2264
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Correa, A.1
Tellitu, I.2
Domínguez, E.3
Moreno, I.4
SanMartin, R.5
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28
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38649140735
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note
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At higher dilution, the reaction time was prolonged excessively.
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29
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38649098821
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note
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Diesters 3a-e were identified by the aid of selective TOCSY experiments from the crude reaction prior to the addition of silica gel. See selected information in Table 1.
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30
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30744475459
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The oxidation of alkenes to carbonyl compounds catalyzed by palladium(II) salts (known as the Wacker reaction) normally proceeds with Markovnikov regioselectivity. For a novel anti-Markovnikov regioselectivity (leading to aldehydes from terminal olefins) in the Wacker reaction of styrenes, see: and more recently
-
The oxidation of alkenes to carbonyl compounds catalyzed by palladium(II) salts (known as the Wacker reaction) normally proceeds with Markovnikov regioselectivity. For a novel anti-Markovnikov regioselectivity (leading to aldehydes from terminal olefins) in the Wacker reaction of styrenes, see:. Wright J.A., Gaunt M.J., and Spencer J.B. Chem.-Eur. J. 12 (2005) 949-955 and more recently
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(2005)
Chem.-Eur. J.
, vol.12
, pp. 949-955
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Wright, J.A.1
Gaunt, M.J.2
Spencer, J.B.3
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32
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4644234793
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The catalytic anti-Markovnikov hydration of terminal alkynes to aldehydes has been also described. See:
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The catalytic anti-Markovnikov hydration of terminal alkynes to aldehydes has been also described. See:. Grotjahn D.B., and Lev D.A. J. Am. Chem. Soc. 126 (2004) 12232-12233
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(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 12232-12233
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Grotjahn, D.B.1
Lev, D.A.2
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33
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21244435594
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Phenylacetaldehyde (4a) is a common byproduct also obtained directly during the oxidation of styrene into styrene oxide by a number of reaction conditions. For a recent example, see:
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Phenylacetaldehyde (4a) is a common byproduct also obtained directly during the oxidation of styrene into styrene oxide by a number of reaction conditions. For a recent example, see:. Zhang J.-L., and Che C.-M. Chem.-Eur. J. 11 (2005) 3899-3914
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(2005)
Chem.-Eur. J.
, vol.11
, pp. 3899-3914
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Zhang, J.-L.1
Che, C.-M.2
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34
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0032514970
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3 to afford the corresponding arylacetaldehydes in good yields. See:
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3 to afford the corresponding arylacetaldehydes in good yields. See:. Ranu B.C., and Jana U. J. Org. Chem. 63 (1998) 8212-8216
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(1998)
J. Org. Chem.
, vol.63
, pp. 8212-8216
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Ranu, B.C.1
Jana, U.2
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35
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0000614776
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Koser reported a similar alteration of the regioselectivity using HTIB. See:
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Koser reported a similar alteration of the regioselectivity using HTIB. See:. Koser G.F. J. Org. Chem. 46 (1981) 4324-4326
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(1981)
J. Org. Chem.
, vol.46
, pp. 4324-4326
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Koser, G.F.1
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36
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13844266930
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Another example of the use of hypervalent iodine reagents under solvent-free conditions can be found in:
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Another example of the use of hypervalent iodine reagents under solvent-free conditions can be found in:. Yusubov M.S., and Wirth T. Org. Lett. 7 (2005) 519-521
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(2005)
Org. Lett.
, vol.7
, pp. 519-521
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Yusubov, M.S.1
Wirth, T.2
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38
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38649085372
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note
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It must be pointed out that a control experiment carried out with styrene 1c using PIDA [phenyliodine(III) diacetate], instead of PIFA, under the same reaction conditions resulted in the recovery of the starting material completely unchanged. This result evidences the superior activity of PIFA over PIDA.
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39
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33845553556
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For spectroscopic information of aldehyde 4b, see:
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For spectroscopic information of aldehyde 4b, see:. Miyaura N., Maeda K., and Suginome H. J. Org. Chem. 47 (1982) 2117-2120
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(1982)
J. Org. Chem.
, vol.47
, pp. 2117-2120
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Miyaura, N.1
Maeda, K.2
Suginome, H.3
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40
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0032514970
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For 4c,d, see:
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For 4c,d, see:. Ranu B.C., and Jana U. J. Org. Chem. 63 (1998) 8212-8216
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(1998)
J. Org. Chem.
, vol.63
, pp. 8212-8216
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Ranu, B.C.1
Jana, U.2
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42
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0001613419
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6 times higher than the triflate group in the particular reaction of a phenyliodonium salt.
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6 times higher than the triflate group in the particular reaction of a phenyliodonium salt. Okuyama T., Takino T., Sueda T., and Ochiai M. J. Am. Chem. Soc. 117 (1995) 3360-3367
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(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 3360-3367
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-
Okuyama, T.1
Takino, T.2
Sueda, T.3
Ochiai, M.4
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43
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38649114102
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note
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In these cases, donating methoxy groups are placed at 2- and 4-positions, an electronic feature required to stabilize positively charged species III. Consequently, the methoxy group located at the meta position in styrene 1d disfavors the stability of intermediate III, which explains the dramatic decrease in the yield for its transformation into 4d.
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52
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0141854098
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Boye A.C., Meyer D., Ingison C.K., French A.N., and Wirth T. Org. Lett. 5 (2003) 2157-2159
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(2003)
Org. Lett.
, vol.5
, pp. 2157-2159
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Boye, A.C.1
Meyer, D.2
Ingison, C.K.3
French, A.N.4
Wirth, T.5
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54
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38649118243
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See also Ref. 9b.
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See also Ref. 9b.
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-
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55
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38649102859
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In both cases, olefins 1h,i required 12-14 h for their complete conversion instead of the standard 3-4 h;
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In both cases, olefins 1h,i required 12-14 h for their complete conversion instead of the standard 3-4 h;
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-
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56
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38649138359
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Aliphatic olefins behave in a similar way with PIFA to afford 1,2-bistrifluoroacetates. See Ref. 6;
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Aliphatic olefins behave in a similar way with PIFA to afford 1,2-bistrifluoroacetates. See Ref. 6;
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-
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57
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0038512211
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4 in methanol. For spectroscopic data of diol 6h, see:
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4 in methanol. For spectroscopic data of diol 6h, see:. Tanaka Y., Nishimura K., and Tomioka K. Tetrahedron 59 (2003) 4549-4556
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(2003)
Tetrahedron
, vol.59
, pp. 4549-4556
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Tanaka, Y.1
Nishimura, K.2
Tomioka, K.3
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58
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17944377190
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For diol 6i, see:
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For diol 6i, see:. Pinard E., Alanine A., Bourson A., Büttelmann B., Gill R., Heitz M.P., Jaeschke G., Mutel V., Trube G., and Wyler R. Bioorg. Med. Chem. Lett. (2001) 2173-2176
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(2001)
Bioorg. Med. Chem. Lett.
, pp. 2173-2176
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Pinard, E.1
Alanine, A.2
Bourson, A.3
Büttelmann, B.4
Gill, R.5
Heitz, M.P.6
Jaeschke, G.7
Mutel, V.8
Trube, G.9
Wyler, R.10
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60
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0242415168
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For diol 7i, see:
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For diol 7i, see:. Katz C.E., and Aubé J. J. Am. Chem. Soc. 125 (2003) 13948-13949
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(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 13948-13949
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Katz, C.E.1
Aubé, J.2
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61
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33747391903
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Carbonyl compounds 4j-l were spectroscopically identified by comparison with the reported data. For ketone 4j, see:
-
Carbonyl compounds 4j-l were spectroscopically identified by comparison with the reported data. For ketone 4j, see:. Khanh-Van Tran K.-V., and Bickar D. J. Org. Chem. 71 (2006) 6640-6643
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(2006)
J. Org. Chem.
, vol.71
, pp. 6640-6643
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Khanh-Van Tran, K.-V.1
Bickar, D.2
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62
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33847677168
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For 4k, see:
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For 4k, see:. Molinaro C., Mowat J., Gosselin F., O'Shea P.D., Marcoux J.F., Angelaud R., and Davies I.W. J. Org. Chem. 72 (2007) 1856-1858
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(2007)
J. Org. Chem.
, vol.72
, pp. 1856-1858
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Molinaro, C.1
Mowat, J.2
Gosselin, F.3
O'Shea, P.D.4
Marcoux, J.F.5
Angelaud, R.6
Davies, I.W.7
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64
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38649142494
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note
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At this stage, there is no clear explanation to the fact that no 1,2-addition of trifluoroacetate groups to styrene 1j is detected, as it would have been anticipated considering the lack of activation of the phenyl ring.
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