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For exceptions to this general trend, see: a
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Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 4, p 585.
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35048840884
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For reactions of the neutral or anionic form of this nucleophile with two allylic carbonates, see refs 5 and 6
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For reactions of the neutral or anionic form of this nucleophile with two allylic carbonates, see refs 5 and 6.
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35048829002
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Ring-closing metathesis of related materials after formation of the HBr salt has been reported to occur in good yield ref 6
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Ring-closing metathesis of related materials after formation of the HBr salt has been reported to occur in good yield (ref 6).
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84858344456
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$0.78/g from Aldrich
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$0.78/g from Aldrich.
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The linear monoallylation product could not be observed clearly in the 1H NMR spectrum, and could not be quantified. Thus, we do not report branched-to-linear selectivities for these reactions. Several signals corresponding to a majority of the mass balance were observed in the region of the 1H NMR spectrum in which the allylic hydrogens of linear products resonate, perhaps from formation of regioisomeric diallylation products. Nevertheless, these side products were easily removed from the branched product by flash chromatography, and good yields of the pure branched product were obtained. A larger excess of potassium trifluoroacetamide (2.4 equiv) increased the reaction rate and lowered the intensity of the resonances proposed to result from regioisomeric side products; however, it also increased the rate of decomposition of the carbonate to alcohol and did not measurably improve the overall yield
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1H NMR spectrum in which the allylic hydrogens of linear products resonate, perhaps from formation of regioisomeric diallylation products. Nevertheless, these side products were easily removed from the branched product by flash chromatography, and good yields of the pure branched product were obtained. A larger excess of potassium trifluoroacetamide (2.4 equiv) increased the reaction rate and lowered the intensity of the resonances proposed to result from regioisomeric side products; however, it also increased the rate of decomposition of the carbonate to alcohol and did not measurably improve the overall yield.
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