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(i) For a review, see: Kiplinger, J. L.; Richmond, T. G.; Osterbera, C. E. Chem. Rev. 1994, 94, 341. (j) Allmer, K.; Feiring, A. E. Macromolecules 1991, 24, 5487. (k) Kaprinidis, N. A.; Turro, N. J. Personal communication, 1995.
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20
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85033846766
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note
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(a) Compare the electron affinities of hexafluorobenzene (0.51 eV) and perfluorocyclohexene (>1.4 eV).
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21
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33845374128
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(b) Chowdhury, S.; Grimsrud, E. P.; Heinis, T.; Kebarle, P. J. Am. Chem. Soc. 1986, 108, 3630.
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Bowers, M. T., Ed.; Academic Press: Orlando, FL
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37049095824
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(d) Kolenko, I. P.; Filyakova, T. I.; Zapelov, A. Y.; Lur'e, E. P. Izv. Akad. Nauk SSSR. Ser. Khim. 1979, 2509.
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Lur'e, E.P.4
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28
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85033841020
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note
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4 and distilled (59-61 °C). The UV spectra of all starting materials showed that unsaturation was completely absent.
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29
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85033849424
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note
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3).
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31
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4244094414
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(c) Campbell, S. F.; Hudson, A. G.; Mooney, E. F.; Pedler, A. E.; Stevens, R.; Wood, K. N. Spectrochim. Acta 1967, 23A, 2119.
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Campbell, S.F.1
Hudson, A.G.2
Mooney, E.F.3
Pedler, A.E.4
Stevens, R.5
Wood, K.N.6
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32
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0012431943
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(a) Derek, J.; Burdon, J.; Carter, P. A.; Patrick, C. R.; Tatlow, J. C. J. Fluorine Chem. 1982. 21 (3), 305.
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Derek, J.1
Burdon, J.2
Carter, P.A.3
Patrick, C.R.4
Tatlow, J.C.5
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34
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85033836126
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note
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2 solution.
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36
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85033856332
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note
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We avoided powdered Zn because it tends to absorb light.
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37
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85033867872
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note
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6 solution showed new resonances at -59.41 (s, br, 3F), -61.9 (m, 3F), -85.1 (s, 3F), -118.5 (dd, J = 17.1, 1F), -98.8 (m, 2F) corresponding to perfluoro-2-methyl-2-pentene, as verified by comparison with a commercial sample (Aldrich). UV (THF) = 226 (110).
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38
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85033836298
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note
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2): 5.7 (br, 2H), 10.6 (br, 1H), UV (EtOH): 274 (16 400).
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40
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85033860113
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note
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3.
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41
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85033849198
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note
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3 gave 4 and 4′ (310 mg, 0.93 mmol, 60%).
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