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note
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Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-142652 (5d) and -149648 (5i). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
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19
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17344367543
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It is well-known that the 1,5-hydrogen shift in many substituted cyclopentadienes is fast even at room temperature. For a detailed discussion of thermal sigmatropic rearrangements, including 1,5-hydrogen shifts, see: C. W. Spangler, Chem. Rev. 1976, 76, 187-217.
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Wiley, London
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It is well documented that a donor substituent activates a 1,3-diene more when placed in the 1-position than in the 3-position, and a dimethylamino group is a more efficient donor than an ethoxy group. For a detailed discussion, see: I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, London, 1976.
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Fleming, I.1
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22
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33845551817
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Both the steric and the electronic effects play an important role for the facial stereoselectivity of the Diels-Alder reaction of substituted cyclopentadienes with dienophiles. For a detailed discussion, see: R. Gleiter, L. A. Paquette, Acc. Chem. Res. 1983, 16, 328-334.
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L. Brandsma, S. F. Vasilevsky, H. D. Verkruijsse, Application of Transition Metal Catalysis in Organic Synthesis, Springer, Berlin, 1999.
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