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[1d] V. Breitkopf, H. Hopf, F.-G. Klärner, B. Witulski, B. Zimny, Liebigs Ann. 1995, 613-617.
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[2b] D. J. Cram, C. S. Montgomery, G. R. Knox, J. Am. Chem. Soc. 1966, 88, 515-525.
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33749091346
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note
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[5e]).
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14
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0842341771
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[5b] M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909.
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84988129057
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[5c] J. J. P. Stewart, J. Comput. Chem. 1989, 10, 209-214, 221-232. The AM1 and PM3 calculations were performed by the use of SPARTAN 3.1 distributed by W. J. Hehre and L. D. Burke, Wave function, Inc. 18401 Von Karman, Suite 370, Irvine, California, 92715, USA.
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Stewart, J.J.P.1
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Chapman and Hall Ltd., London
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[5e] J. P. Pedley, R. D. Naylor, S. P. Kirby, Thermochemical Data of Organic Compounds, 2nd ed., Chapman and Hall Ltd., London 1986.
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18
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0001641572
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2] cycloaddition, which is precedented only in photochemical reaction: K. E. Wilzbach, L. Kaplan, J. Am. Chem. Soc. 1966, 88, 2066-2075;
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Wilzbach, K.E.1
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13944250372
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V. Y. Merrit, J. Cornelisse, R. Srinivasan, J. Am. Chem. Soc. 1973, 95, 8250-8257;
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0000148013
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W. Ferree Jr., J. P. Grutzner, H. Morrison, J. Am. Chem. Soc. 1971, 93, 5502-5508;
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Ferree Jr., W.1
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84988072787
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A = 35.4 kcal/mol, logA = 14.0). F.-G. Klärner, S. Yaslak, R. Drewes, Ch. Gesenberg, M. Peter, Liebigs Ann. 1995, 203-210.
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Klärner, F.-G.1
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Peter, M.5
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26
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33749102438
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The competing [2 + 2] cycloaddition and homo Diels-Alder cycloaddition of tetrachlorobenzene and parent benzyne also show no significant pressure dependence. These results were considered to be indicative of the stepwise mechanism of the homo Diels-Alder reaction: W. J. LeNoble, R. Mukhtar, J. Am. Chem. Soc. 1974, 96, 6191-6192;
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LeNoble, W.J.1
Mukhtar, R.2
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0040891969
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F.-G. Klärner, B. Krawczyk, V. Ruster, U. K. Deiters, J. Am. Chem. Soc. 1994, 116, 7646-7657.
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Klärner, F.-G.1
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Deiters, U.K.4
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28
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33749086577
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note
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o = 176.3 - 178.6 = -2.3 kcal/mol).
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29
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4544279012
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G. H. Viehe, R. Merényi, J. F. M. Oth, P. Valange, Angew. Chem. 1964, 76, 888-889;
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Viehe, G.H.1
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4544237383
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G. H. Viehe, R. Merényi, J. F. M. Oth, R. Senders, P. Valange, Angew. Chem. 1964, 76, 923-924;
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Viehe, G.H.1
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84984318596
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(Chem. Abstr. 1946, 42, P6847);
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Chem. Abstr.
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42
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84943866543
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S. Murahashi, T. Takizawa, S. Kurioka, S. Maekawa, Nippon Kagaku Zasshi 1956, 77, 1689-1692;
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Murahashi, S.1
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Maekawa, S.4
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44
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33749093167
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note
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The isocoumarinophane 12 has also been obtained by Vögtle in an attempt to decarbonylate 6 at 620°C over quartz wool. Presumably the compound is formed by enolization of the ketone and subsequent addition of the OH function to the neighboring cyano group. From the resulting cyclic imidoester, 12 could be formed by hydrolysis during work-up: F. Vögtle, private communication, November 1992.
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