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[4+3] cycloaddition reactions
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85039513485
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note
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Prepared from 3-bromofuran by lithiation and reaction with ethylene oxide followed by conversion to the bromide and then the Grignard reagent. See the Experimental Section for details.
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For example, the yield of Kolbe dimerization is enhanced at high current densities: Coleman, J. P.; Lines, R.; Utley, J. H. P. J. Chem. Soc., Perkin Trans. 2 1973, 1064.
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85039522348
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note
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We have found that the furyl ketone products are very susceptible to air oxidation at the activated bridgehead position and cannot be stored for long periods of time. Purging of chromatography and other solvents improves the yield by 10-15%. Subsequent reduction or ketalization of the ketone eliminates this problem.
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3-Bromofuran is commercially available or can be prepared from furan as in: (a) Politis, J. K.; Nemes, J. C.; Curtis, M. D. J. Am. Chem. Soc. 2001, 123, 2537.
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