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Hamada H., Shiromoto M., Funahashi M., Itoh T., and Nakamura K. J. Org. Chem. 61 (1996) 2332
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14
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33947462538
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When ethyl trichloroacetate was added to an ethereal solution of PhMgBr (4 equiv) at 0 °C and then refluxing for 1.5 h furnished an almost quantitative amount of PhCl, see:
-
When ethyl trichloroacetate was added to an ethereal solution of PhMgBr (4 equiv) at 0 °C and then refluxing for 1.5 h furnished an almost quantitative amount of PhCl, see:. Kaluszyner A., and Reuter S. J. Am. Chem. Soc. 75 (1953) 5126
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Kaluszyner, A.1
Reuter, S.2
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15
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38649098512
-
-
note
-
In Ref. 2, Creary reported basically identical result for the reaction of PhMgBr and ethyl acetate in ether at -78 °C, followed by warming to rt leading to the exclusive formation of the tertiary alcohol 1,1-diphenylethanol in 96% yield.
-
-
-
-
16
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0002204826
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For the MPV reductions using fluorine-containing substrates, see:. Fleming I., and Trost B.M. (Eds), Pargamon, Oxford
-
For the MPV reductions using fluorine-containing substrates, see:. Kellogg R.M. In: Fleming I., and Trost B.M. (Eds). Comprehensive Organic Synthesis (1991), Pargamon, Oxford 88
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Comprehensive Organic Synthesis
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Kellogg, R.M.1
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18
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29144518060
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Sokeirik Y.S., Sato K., Omote M., Ando A., and Kumadaki I. J. Fluorine Chem. 127 (2006) 150
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Sokeirik, Y.S.1
Sato, K.2
Omote, M.3
Ando, A.4
Kumadaki, I.5
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19
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33644992892
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Sokeirik Y.S., Sato K., Omote M., Ando A., and Kumadaki I. Tetrahedron Lett. 47 (2006) 2821
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Tetrahedron Lett.
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Sokeirik, Y.S.1
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Ando, A.4
Kumadaki, I.5
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20
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38649084130
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-
note
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Although this yield should be theoretically zero, a small amount of contaminant might cause this reaction.
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21
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15744375697
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*) level of theory., Gaussian, Wallingford, CT
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*) level of theory. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision B.03 (2004), Gaussian, Wallingford, CT
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Gaussian 03, Revision B.03
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Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, J.R.6
Montgomery Jr., J.A.7
Vreven, T.8
Kudin, K.N.9
Burant, J.C.10
Millam, J.M.11
Iyengar, S.S.12
Tomasi, J.13
Barone, V.14
Mennucci, B.15
Cossi, M.16
Scalmani, G.17
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Petersson, G.A.19
Nakatsuji, H.20
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Ehara, M.22
Toyota, K.23
Fukuda, R.24
Hasegawa, J.25
Ishida, M.26
Nakajima, T.27
Honda, Y.28
Kitao, O.29
Nakai, H.30
Klene, M.31
Li, X.32
Knox, J.E.33
Hratchian, H.P.34
Cross, J.B.35
Bakken, V.36
Adamo, C.37
Jaramillo, J.38
Gomperts, R.39
Stratmann, R.E.40
Yazyev, O.41
Austin, A.J.42
Cammi, R.43
Pomelli, C.44
Ochterski, J.W.45
Ayala, P.Y.46
Morokuma, K.47
Voth, G.A.48
Salvador, P.49
Dannenberg, J.J.50
Zakrzewski, V.G.51
Dapprich, S.52
Daniels, A.D.53
Strain, M.C.54
Farkas, O.55
Malick, D.K.56
Rabuck, A.D.57
Raghavachari, K.58
Foresman, J.B.59
Ortiz, J.V.60
Cui, Q.61
Baboul, A.G.62
Clifford, S.63
Cioslowski, J.64
Stefanov, B.B.65
Liu, G.66
Liashenko, A.67
Piskorz, P.68
Komaromi, I.69
Martin, R.L.70
Fox, D.J.71
Keith, T.72
Al-Laham, M.A.73
Peng, C.Y.74
Nanayakkara, A.75
Challacombe, M.76
Gill, P.M.W.77
Johnson, B.78
Chen, W.79
Wong, M.W.80
Gonzalez, C.81
Pople, J.A.82
more..
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23
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0035801609
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13C NMR chemical shifts of 3a (δ 179.59 (q, J=34 Hz)) and 3e (δ 197.94), clearly indicating more deshielded circumstance of the carbonyl carbon atom of 3e, see:
-
13C NMR chemical shifts of 3a (δ 179.59 (q, J=34 Hz)) and 3e (δ 197.94), clearly indicating more deshielded circumstance of the carbonyl carbon atom of 3e, see:. Asao N., Asano T., and Yamamoto Y. Angew. Chem., Int. Ed. 40 (2001) 3206
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Angew. Chem., Int. Ed.
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Asao, N.1
Asano, T.2
Yamamoto, Y.3
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25
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38649107867
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note
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A small amount of the aldol product (ca. 5% yield) was also detected in the case of trifluorinated case. The similar situation was occurred for the related system in Ref. 7b.
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-
-
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27
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38649095260
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note
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-1 for 13e.
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-
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29
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36649036322
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Moreover, Oppenauer oxidation by using the high electrophilicity of trifluoroacetone was also reported.
-
Moreover, Oppenauer oxidation by using the high electrophilicity of trifluoroacetone was also reported. Mello R., Martínez-Ferrer J., Asensio G., and González-Núñez M.E. J. Org. Chem. 72 (2007) 9376
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J. Org. Chem.
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Mello, R.1
Martínez-Ferrer, J.2
Asensio, G.3
González-Núñez, M.E.4
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32
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38649121503
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Kitazume, T.; Takeda, M. Jpn. Kokai Tokkyo Koho JP 01233244, 1989.
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Kitazume, T.; Takeda, M. Jpn. Kokai Tokkyo Koho JP 01233244, 1989.
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34
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20444472366
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Song J.J., Tan Z., Reeves J.T., Gallou F., Yee N.K., and Senanayaka C.H. Org. Lett. 7 (2005) 2193
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Song, J.J.1
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Senanayaka, C.H.6
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