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See also
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See also:
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113
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77949569916
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note
-
A significative increase in yield of the domino sequence has been obtained since the publication of our preliminary communication, from 41% to 54% (over three steps, average of 81% per step).
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For a review, see
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126
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18944394614
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For a recent example of an alteration of tubulin polymerization activity by nitroxyl donors, see:
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77949569088
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The reaction of acetone oxime and cyclohexanone oxime with lead tetraacetate in dichloromethane afforded the corresponding α-acetoxynitroso derivatives in only 33 and 37% isolated yield. The residual acetic acid in lead tetraacetate led to considerable amount of hydrolysis of the α-acetoxynitroso moiety.
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132
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For an alternative recent synthesis, see .
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For an alternative recent synthesis, see Ref. 34.
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Lead tetraacetate toxicity is a well established phenomena, for recent references, see
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Lead tetraacetate toxicity is a well established phenomena, for recent references, see:
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Silbergeld E.K. Mutat. Res. 533 (2003) 121. http://www.sigmaaldrich.com On the other hand, iodobenzene diacetate was found to be not hazardous to humans and the environment according to Directive 67/548/EEC
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2O donor and as a base (see: To rule out any influence of the powdered 4 Å molecular sieves in yield variability, experiments were run in their absence. However, product distribution and yields were still highly variable with or without molecular sieves leading us to discard sieves as a major cause of non-reproducibility
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2O donor and as a base (see:. Terada M., Matsumoto Y., Nakamura Y., and Mikami K. Chem. Commun. (1997) 281 To rule out any influence of the powdered 4 Å molecular sieves in yield variability, experiments were run in their absence. However, product distribution and yields were still highly variable with or without molecular sieves leading us to discard sieves as a major cause of non-reproducibility
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See Supporting data.
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147
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77949571018
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note
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Experimentally, we have observed that dienophile 43 was much less stable than dienophile 32 in the presence of a Lewis acid or an aqueous HCl solution (1 N).
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The reported results indicate that the addition of Lewis acids decreases the rate of the cycloaddition reaction of α-acyloxynitroso derivatives. It is worth noting that the rate-determining step of this cycloaddition might not involve Lewis acid and that the observed low enantiomeric excess might be the result of an enantioselective Lewis acid opening of the cycloadduct. We wish to thank a reviewer for suggesting this possibility.
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For the General information, see Supporting data
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For the General information, see Supporting data.
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