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0040715906
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Thermolysis of 2a at 110°C for 10 days to give the isomeric benzo-[b]fluorenols 4a (44%) and 5a (13%) had been previously described: Schmittel, M.; Strittmatter, M.; Schenk, W. A.; Hagel, M. Z. Naturforsch 1998, 53b, 1015-1020.
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(a) Danheiser, R. L.; Gould, A. E.; Fernández de la Pradilla, R.; Helgason, A. L. J. Org. Chem. 1994, 59, 5514-5515.
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(c) González, J. J.; Francesch, A.; Cárdenas, D. J.; Echavarren, A. M. J. Org. Chem. 1998, 63, 2854-2857.
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(b) Miyawaki, K.; Suzuki, R.; Kawano, T.; Ueda, I. Tetrahedron Lett. 1997, 38, 3943-3946.
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18
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0442330934
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note
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Benzo[b]fluorenones 4b and 5b had been obtained previously as byproducts when studying thermolysis of 2a at 110°C. See ref 2.
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19
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0442330933
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note
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See Supporting Information for experimental details.
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21
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33748240634
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For a theoretical study of 1,2,4-cyclohexatriene, a conjugated cyclic allene, see: Janoschek, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 476-478.
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Janoschek, R.1
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23
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0004133516
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Gaussian, Inc., Pittsburgh, PA
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All calculations were performed with the Gaussian 98 and Gaussian 94 program packages. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A. Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; González, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh, PA, 1998.
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Gaussian 98, Revision A.7
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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 Jr., J.A.8
Stratmann, R.E.9
Burant, J.C.10
Dapprich, S.11
Millam, J.M.12
Daniels, A.D.13
Kudin, K.N.14
Strain, M.C.15
Farkas, O.16
Tomasi, J.17
Barone, V.18
Cossi, M.19
Cammi, R.20
Mennucci, B.21
Pomelli, 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
Baboul, A.G.36
Stefanov, B.B.37
Liu, G.38
Liashenko, A.39
Piskorz, P.40
Komaromi, I.41
Gomperts, R.42
Martin, R.L.43
Fox, D.J.44
Keith, T.45
Al-Laham, M.A.46
Peng, C.Y.47
Nanayakkara, A.48
Gonzalez, C.49
Challacombe, M.50
Gill, P.M.W.51
Johnson, B.52
Chen, W.53
Wong, M.W.54
Andres, J.L.55
González, C.56
Head-Gordon, M.57
Replogle, E.S.58
Pople, J.A.59
more..
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25
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0345491105
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Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
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Phys. Rev. B
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Lee, C.1
Yang, W.2
Parr, R.G.3
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26
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0033595573
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and references therein
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Although pure functionals have recently been used for description of species with biradical character, we achieved better results using hybrid functionals. Schreiner, P. R.; Prall, M. J. Am. Chem. Soc. 1999, 121, 8615-8627 and references therein.
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Schreiner, P.R.1
Prall, M.2
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29
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0442299745
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note
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The combination of these two factors was inferred using MCSCF and B3LYP calculations for the models (Z)-4-heptene-1,6-diyn-3-one and (Z)-3-heptene-1,6-diyne. Results to be published elsewhere.
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30
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0011083499
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Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
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Chem. Rev.
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Reed, A.E.1
Curtiss, L.A.2
Weinhold, F.3
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32
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0442299744
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Results to be published elsewhere
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Results to be published elsewhere.
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33
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0442283881
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note
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This hypothesis had been suggested previously by Danheiser et al. See ref 5a.
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34
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0442283880
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note
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Increased yield in the presence of a proton source (ArOH) has been observed previously in intramolecular [4 + 2] cycloadditions. See ref 5a.
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