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S. Y. Wang and W. T. Borden, J. Am. Chem. Soc., 1989, 111, 72827283; S. J. Getty and W. T. Borden, J. Am. Chem. Soc., 1991, 113, 4334-4335. Borden shows that the low reactivity of tetrafluoroethylene in [4 + 2] cycloaddition reactions arises from the facility with which it undergoes [2 + 2] cycloadditions via biradical pathways. Alkene ground state destabilisation and biradical stabilisation contribute to the effect.
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note
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Reference 20b reviews related Brønsted and Lewis acid-mediated ring openings of the oxabicyclo[2.2.1]heptenyl template.
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M. Lautens and W. Klute, Angew. Chem., Int. Ed. Engl., 1996, 35, 442-445.
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Oishi, S.1
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S. Oishi, T. Kamano, A. Niida, Y. Odagaki, H. Tamamura, A. Otaka, N. Hamanaka and N. Fujii, Org. Lett., 2002, 4, 1051-1054; A. Otaka, H. Watanabe, A. Yukimasa, S. Oishi, H. Tamamura and N. Fujii, Tetrahedron Lett., 2001, 42, 5443-5446.
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Many of the literature examples take place upon symmetrical systems so electronic influences upon the hydrostannylation reaction have not been defined. For an attempt to detect such influences upon carbopalladtion reactions of the oxabicyclo[2.2.1]heptenyl template, see : C. Montalbetti, M. Savignac, J.-P. Gênet, J.-M. Roulet and P. Vogel, Tetrahedron Lett., 1996, 37, 2225-2228.
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Vogel, P.5
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ed.R. J. K Taylor, Oxford University Press, Oxford
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