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A transition structure with the oxygen on the flap of the envelope and the C2′ and C5′ substituents in the equatorial positions would provide the same product. See ref 11a
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A transition structure with the oxygen on the flap of the envelope and the C2′ and C5′ substituents in the equatorial positions would provide the same product. See ref 11a.
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The numbering scheme changes from the cyclopropane starting material going to the tetrahydrofuran product. The prime (′) denotes an atom in the product
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The numbering scheme changes from the cyclopropane starting material going to the tetrahydrofuran product. The prime (′) denotes an atom in the product.
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A reviewer suggested that our results may still be interpreted as an SN2 mechanism. We believe that the high site selectivity in the cycloaddition of compound 16 provides the best evidence against the SN2 mechanism. Because the SN1/SN2 continuum contains reactions proceeding via intimately associated ion pairs, the most complete description consistent with the IUPAC nomenclature for such reactions would be DN*ANint. For excellent reviews of substitution mechanisms, see: (a) Guthrie, R. D, Jencks, W. P. Acc. Chem. Res. 1989, 22, 343-349
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Nint. For excellent reviews of substitution mechanisms, see: (a) Guthrie, R. D.; Jencks, W. P. Acc. Chem. Res. 1989, 22, 343-349.
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