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5
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15844365659
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1 in Figure 1b in this paper, which is reported to be preferred by an equatorial acetate, is what is now called eclipsed, a word not used by the author. His Figure 4 refers to "esters attached to the ring by a polar oxygen" meaning what is now called an axial acetate, which likewise on the basis of "a few examples" prefers an eclipsed exocyclic bond. It is now little recalled that rather than "axial", "polar" was first suggested.
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(f) Anderson, J. E.; Angyal, S. J.; Craig, D. C. J. Chem. Soc., Perkin Trans. 2 1997, 729-734.
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16
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17044378486
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note
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7a
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17
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17044401286
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note
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The extended arrangement 9 is clearly present in the preferred conformation of many cyclic molecules. In all but a few acyclic molecules, however, rotation about the C2-C3 or C3-C4 bond will lead to a more stable molecular conformation where interactions of R with A or B are removed, and thus eclipsing of the C-O bond is not helpful.
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19
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0025239934
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Anet has given another general definition of axial and equatorial that is much less useful for the present study, since it is based on distances derived from experimental or calculated data rather than on directly reported torsion angles: Anet, F. A. L. Tetrahedron Lett. 1990, 31, 2125-2126
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Anet, F.A.L.1
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(a) Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8551-8566.
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23
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17044433801
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note
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Conformations of compound 18 where an isopropyl group has rotated to place a hydrogen at position A or B, see 8, are calculated to be at least 2.85 kcal/mol less stable than the conformation shown.
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24
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0002365919
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The Exo-Anomeric Effect
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Szarek, W. A., Horton, D., Eds.; ACS Symposium Series 87; American Chemical Society: Washington, D.C.
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25
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0001825704
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27
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0000240610
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0001166581
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29
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17044410830
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note
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12 is 143.5 pm whereas the C-C bond length is 151.5pm.
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30
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0344236076
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