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ed. A. Ricci, Wiley-VCH, Weinheim
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78049342771
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2 and a sulfamate, led to the formation of the corresponding C-H aminated product with a low yield of 18%
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2 and a sulfamate, led to the formation of the corresponding C-H aminated product with a low yield of 18%.
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79
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78049329851
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A test experiment starting from the homolog 1,4-diphenylbutane did not afford the corresponding C-H aminated product
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A test experiment starting from the homolog 1,4-diphenylbutane did not afford the corresponding C-H aminated product.
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80
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78049330864
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The observed ratio of 70% could have been attributed to the diastereoselective formation of regioisomers. However, this hypothesis was ruled out in the case of 6g by removing the o-bromo substituent under reductive conditions. This transformation was shown to give 6b as a mixture of isomers with a d.e. of 70%. Had we previously isolated regioisomers, this transformation would have led to a single product
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The observed ratio of 70% could have been attributed to the diastereoselective formation of regioisomers. However, this hypothesis was ruled out in the case of 6g by removing the o-bromo substituent under reductive conditions. This transformation was shown to give 6b as a mixture of isomers with a d.e. of 70%. Had we previously isolated regioisomers, this transformation would have led to a single product.
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85
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0003674116
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E. L. Eliel, S. H. Wilen and M. P. Doyle, Wiley Interscience, New York, 495 Should the kinetic resolution operate in the absence of the equilibrium between the enantiomeric iminoiodanes 16, no more than 55% of C-H aminated product will be isolated.
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We are currently investigating whether the formation of diastereoisomers results from C-H amination of the two interconverting chair conformations of cis-decalin 14 which are not identical but enantiomers. See: Basic Organic Stereochemistry, E. L. Eliel, S. H. Wilen, and, M. P. Doyle, Wiley Interscience, New York, 2001, p. 495
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(2001)
Basic Organic Stereochemistry
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87
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78049331038
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It should be pointed out that an unknown product resulting from a reaction between the metallanitrene and BHT was also isolated in the case of 2-methylbutane (yield in the 20-25% range). This could be responsible for the lower yield observed
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It should be pointed out that an unknown product resulting from a reaction between the metallanitrene and BHT was also isolated in the case of 2-methylbutane (yield in the 20-25% range). This could be responsible for the lower yield observed
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92
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78049332185
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2 = 0.91)
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2 = 0.91).
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