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1
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0347627113
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in press
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Chemistry in Superacids. Part 65. For part 64, See G. Rasul, G. K. S. Prakash, and G. A. Olah, J. Phys. Chem., A, in press.
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J. Phys. Chem., A
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Rasul, G.1
Prakash, G.K.S.2
Olah, G.A.3
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2
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0037077012
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(a) K. Yu. Koltunov, G. K. S. Prakash, G. Rasul, and G. A. Olah, J. Org. Chem., 2002, 67, 4330.
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J. Org. Chem.
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Koltunov, K.Yu.1
Prakash, G.K.S.2
Rasul, G.3
Olah, G.A.4
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3
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0037073928
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(b) K. Yu. Koltunov, G. K. S. Prakash, G. Rasul, and G. A. Olah, J. Org. Chem., 2002, 67, 8943.
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J. Org. Chem.
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Koltunov, K.Yu.1
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Olah, G.A.4
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4
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0036642742
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(c) K. Yu. Koltunov, G. K. S. Prakash, G. Rasul, and G. A. Olah, Tetrahedron, 2002, 58, 5423.
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Tetrahedron
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Koltunov, K.Yu.1
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Olah, G.A.4
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8
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0012733397
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For a low-temperature generation of substituted ethylene dications bearing electron-donating groups such as an aryl, a hydroxy, a methoxy and a N,N-dihydroxyamino groups or for their reactions with arenes, see (a) G. A. Olah and A. M. White, J. Am. Chem. Soc., 1967, 89, 4752.
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J. Am. Chem. Soc.
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Olah, G.A.1
White, A.M.2
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10
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0012624629
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(c) G. A. Olah, J. L. Grant, and P. W. Westerman, J. Org. Chem., 1975, 40, 2102.
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J. Org. Chem.
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, pp. 2102
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Olah, G.A.1
Grant, J.L.2
Westerman, P.W.3
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12
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0004474274
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and the references cited therein
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(e) T. Ohwada and K. Shudo, J. Org. Chem., 1989, 54, 5227, and the references cited therein.
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J. Org. Chem.
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Ohwada, T.1
Shudo, K.2
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13
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0029111497
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(f) T. Yamazaki, S. Saito, T. Ohwada, and K. Shudo, Tetrahedron Lett., 1995, 36, 5749.
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Tetrahedron Lett.
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Yamazaki, T.1
Saito, S.2
Ohwada, T.3
Shudo, K.4
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14
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7344228964
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(h) D. A. Klumpp, K. Y. Yeung, G. K. S. Prakash, and G. A. Olah, J. Org. Chem., 1998, 63, 4481.
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Klumpp, D.A.1
Yeung, K.Y.2
Prakash, G.K.S.3
Olah, G.A.4
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15
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0033215075
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(g) D. A. Klumpp, S. Lau, M. Garza, G. V. Sanchez, B. Schick, and K. Kantardjieff, J. Org. Chem., 1999, 64, 7635.
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Klumpp, D.A.1
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16
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0001023472
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I. B. Repinskaya, K. Yu. Koltunov, M. M. Shakirov, and V. A. Koptyug, J. Org. Chem., USSR. 1992, 28, 785.
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Repinskaya, I.B.1
Koltunov, K.Yu.2
Shakirov, M.M.3
Koptyug, V.A.4
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17
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0347627109
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Eur. Patent 1990, 356230
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Dications (19-27) were preferred based on the participation of the non-bonded electron pairs of both heteroatoms in charge delocalization (with the exception of 24). Favorable formation of dications (20, 21, 26 and 27) also conforms to positional selectivity of electrophilic substitution reactions of 11 and 13 in strong acids (hydrogen-deuterium exchange, nitration, etc.) to give 6- and 8-substituted 2- and 4-quinolones, see, for example: (a) R. M. Welch, A. R. Brown, and A. P. Phillips, Eur. Patent 1990, 356230.
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Welch, R.M.1
Brown, A.R.2
Phillips, A.P.3
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18
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19644384929
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(b) A. R. Katritzky, B. Terem, E. V. Scriven, S. Clementi, and H. O. Tarhan, J. Chem. Soc., Perkin Trans. II, 1975, 1600. The possibility of additional N-protonation of 11a-13a to give the Corresponding N,N-diprotonated dications was not considered to be kinetically favorable. See, for example, the discussion on that subject for 1- and 2-isoquinolinols: Ref. 2b.
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(1975)
J. Chem. Soc., Perkin Trans. II
, pp. 1600
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Katritzky, A.R.1
Terem, B.2
Scriven, E.V.3
Clementi, S.4
Tarhan, H.O.5
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19
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0004133516
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Gaussian, Inc., Pittsburgh, PA
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M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, R. E. Daniels, K. N. Kudin, M. C. Strain, O. Farcas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelly, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkarra, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Jonson, W. Chen, M. W. Wong, J. L. Andres, C. M. Gonzalez, M. Head-Gordon, and J. A. Pople, Gaussian 98 Revision A.5); Gaussian, Inc., Pittsburgh, PA, 1998.
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Gaussian 98 Revision A.5
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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
Zakrzewski, V.G.7
Montgomery, J.A.8
Stratmann, R.E.9
Burant, J.C.10
Dapprich, S.11
Millam, J.M.12
Daniels, R.E.13
Kudin, K.N.14
Strain, M.C.15
Farcas, O.16
Tomasi, J.17
Barone, V.18
Cossi, M.19
Cammi, R.20
Mennucci, B.21
Pomelly, C.22
Adamo, C.23
Clifford, S.24
Ochterski, J.25
Petersson, G.A.26
Ayala, P.Y.27
Cui, Q.28
Morokuma, K.29
Malick, D.K.30
Rabuck, A.D.31
Raghavachari, K.32
Foresman, J.B.33
Cioslowski, J.34
Ortiz, J.V.35
Stefanov, B.B.36
Liu, G.37
Liashenko, A.38
Piskorz, P.39
Komaromi, I.40
Gomperts, R.41
Martin, R.L.42
Fox, D.J.43
Keith, T.44
Al-Laham, M.A.45
Peng, C.Y.46
Nanayakkarra, A.47
Gonzalez, C.48
Challacombe, M.49
Gill, P.M.W.50
Jonson, B.51
Chen, W.52
Wong, M.W.53
Andres, J.L.54
Gonzalez, C.M.55
Head-Gordon, M.56
Pople, J.A.57
more..
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21
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0000189651
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Becke's three parameter hybrid method using the LYP correlation functional: (a) A. D. Becke, J. Chem. Phys., 1993, 98, 5648.
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(1993)
J. Chem. Phys.
, vol.98
, pp. 5648
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Becke, A.D.1
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22
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0345491105
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(b) C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B, 1988, 37, 785.
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(1988)
Phys. Rev. B
, vol.37
, pp. 785
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Lee, C.1
Yang, W.2
Parr, R.G.3
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23
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33751157732
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(c) P. J. Stephens, F. J. Devlin, C. F. Chabalovski, and M. J. Frisch, J. Phys. Chem., 1994, 98, 11623.
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J. Phys. Chem.
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Stephens, P.J.1
Devlin, F.J.2
Chabalovski, C.F.3
Frisch, M.J.4
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25
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0011083499
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A. E. Reed, L. A. Curtiss, and F. Wienhold, Chem. Rev., 1988, 88, 899.
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Chem. Rev.
, vol.88
, pp. 899
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Reed, A.E.1
Curtiss, L.A.2
Wienhold, F.3
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26
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21844521680
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5 by OR. See: K. Yu. Koltunov, I. B. Repinskaya, M. M. Shakirov, and L. N. Shchegoleva, Russ. J. Org. Chem., 1994, 30, 88.
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(1994)
Russ. J. Org. Chem.
, vol.30
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Koltunov, K.Yu.1
Repinskaya, I.B.2
Shakirov, M.M.3
Shchegoleva, L.N.4
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27
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0346366413
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note
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2 and q•, see, for example, Ref. 2a and 2b.
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28
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0000795644
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Under the reaction conditions cyclohexane exists in an equilibrium with methylcyclopentane, see: C. D. Nenitzescu and R. Cantuniari, Chem. Ber., 1933, 66, 1097.
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(1933)
Chem. Ber.
, vol.66
, pp. 1097
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Nenitzescu, C.D.1
Cantuniari, R.2
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29
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0347627110
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note
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3. See Ref. 2b.
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30
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0346996304
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note
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3 at 25 °C gave in 10% conversion a complex reaction mixture.
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-
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31
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0345735265
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and the references cited therein
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K. M. Johnston, Tetrahedron, 1968, 24, 5595, and the references cited therein.
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(1968)
Tetrahedron
, vol.24
, pp. 5595
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Johnston, K.M.1
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33
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0345735266
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note
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The reaction mixture did not contain compound (11). A single byproduct (∼15%) of the reaction corresponds to the condensation of 35 with phenyl group of product (32).
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36
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0345735264
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German Patent, Hoechst AG, DE 2426851, 1976
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G. Salbeck, German Patent, Hoechst AG, DE 2426851, 1976.
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Salbeck, G.1
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37
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0345735260
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note
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As a mixture of 31/28 (95:5).
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39
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0346366412
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note
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The data are taken from the spectra of mixture of the cis and trans isomers.
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