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33746342608
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note
-
The digit after the decimal in the yields of olefin 2 is not significant. However, the digit after the decimal in the yields of the byproducts (7b, 4, 5, 6, and recovered 1) is significant. Thus, to maintain consistency of presentation, the digit after the decimal is reported for all yields. Note that 100% minus the yield of recovered sulfone 1 is used rather than the yield of olefin 2 in all selectivity calculations. Thus, the legitimacy of including the digit after the decimal is a moot point.
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37
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33746364323
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note
-
See Supporting Information (Appendix) for derivation.
-
-
-
-
39
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0001430734
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2I at below -90 °C, see: Goldstein, M. J.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1965, 87, 2293.
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40
-
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33746355078
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-
note
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1/2 = (t ln(1/2))/(ln(l - M), where t is the time (in seconds) and M is the yield of olefin 2 (expressed in decimal format).
-
-
-
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41
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33746379408
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-
note
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2 (34.3%).
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-
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45
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0028287645
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Hoffmann has shown that the two enantiomers of n-BuCHBrLi do not interconvert at -120 °C: Hoffmann, R. W.; Julius, M.; Chemla, F.; Ruhland, T.; Frenzen, G. Terahedron 1994, 50, 6049.
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Frenzen, G.5
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46
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33746338723
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note
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The stereochemistry of the sulfinate elimination step (syn-coplanar or anti-periplanar) could also be deduced from the absolute configuration of the unreacted, kinetically resolved carbenoid.
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47
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0000446425
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33746362729
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Rappoport, Z., Marek, I., Eds.; John Wiley and Sons: New York, Chapter 13
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77
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33746365258
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note
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2 that has been added.
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78
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Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 2341.
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80
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33746376130
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note
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11Br) could be detected in the crude reaction mixtures by GC. Therefore, no n-octane (product of the Wurtz-Fittig coupling between n-BuLi and n-BuBr) was formed under the conditions of the experiments, thus validating the use of n-octane as internal standard.
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82
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33746334283
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note
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2, 20.13 min. cis- and trans-5-Decene were not sufficiently resolved to permit individual quantitation. Response factors were determined for each component by injection of pure samples purchased from commercial supply houses.
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