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ΔΔG ° = 1.30 kcal/mol for the two chair conformers of methyl cyclohexanecarboxylate, while ΔΔG ° = 0.24 kcal/mol for the two chair conformers of cyclohexanecarbonitrile. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper & Row: New York, 1987.
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25
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0344072293
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note
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s-symmetric diastereomer (not shown) could be isolated when the double Michael reaction was carried out at room temperature.
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-
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27
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0345365729
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note
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Compound 4b can only have a trans ring fusion. If 4b′, 4c, or 4e had a cis ring fusion, the methine H would be equatorial with respect to the B ring in the lower-energy conformer, and a smaller coupling constant to the vicinal trans H would be expected.
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29
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33748593105
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de la Puente, M. L.; Grossman, R. B.; Ley, S. V.; Simmonds, M. S. J.; Blaney, W. M. J. Chem. Soc., Perkin Trans. 1 1996, 1517-1521.
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Simmonds, M.S.J.4
Blaney, W.M.5
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30
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33748612178
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de la Puente, M. L.; Ley, S. V.; Simmonds, M. S. J.; Blaney, W. M. J. Chem. Soc., Perkin Trans. 1 1996, 1523-1529.
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Blaney, W.M.4
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31
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0345365728
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note
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A wide variety of other conditions have also been explored, but the Dieckmann product of 3d has never been obtained in good, reproducible yield.
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-
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32
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0345365727
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-
note
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The stereochemistry was confirmed by coupling constant analysis and a NOESY experiment.
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36
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0013072294
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37
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Fukumoto, K.4
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38
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0344934313
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-
note
-
Preliminary results suggest that the double Michael reaction proceeds with ketoester, cyano ketone, and nitroalkane nucleophiles and with alkynoate and internal alkynone electrophiles.
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