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1
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0004052210
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Oxford University Press, Oxford p. 49
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Harwood L.M. Polar Rearrangements (1992), Oxford University Press, Oxford p. 49
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(1992)
Polar Rearrangements
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Harwood, L.M.1
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2
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0001290085
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Degradation Reactions
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Comprehensive Organic Synthesis - Selectivity. Trost B.M., and Fleming I. (Eds), Pergamon Press, New York
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Shioiri T. Degradation Reactions. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis - Selectivity. Strategy & Efficiency in Modern Organic Chemistry Vols. 6, 4.4 (1991), Pergamon Press, New York 795-828
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(1991)
Strategy & Efficiency in Modern Organic Chemistry
, pp. 795-828
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Shioiri, T.1
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6
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4344670098
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For an example of a benzylic substrate successfully used with DPPA see:
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For an example of a benzylic substrate successfully used with DPPA see:. Spino C., Tremblay M.-C., and Gobdout C. Org. Lett. 6 (2004) 2801-2804
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(2004)
Org. Lett.
, vol.6
, pp. 2801-2804
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Spino, C.1
Tremblay, M.-C.2
Gobdout, C.3
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8
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77951025750
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note
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This byproduct was observed by LC-MS.
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12
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33845282869
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Ohta T., Takaya H., Kitamura M., Nagai K., and Noyori R. J. Org. Chem. 52 (1987) 3174-3176
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(1987)
J. Org. Chem.
, vol.52
, pp. 3174-3176
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Ohta, T.1
Takaya, H.2
Kitamura, M.3
Nagai, K.4
Noyori, R.5
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14
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0001601795
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Manimaran T., Wu T.-C., Klobucar W.D., Kolich C.H., Stahly G.P., Fronczek F.R., and Watkins S.R. Organometallics 12 (1993) 1467-1470
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(1993)
Organometallics
, vol.12
, pp. 1467-1470
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Manimaran, T.1
Wu, T.-C.2
Klobucar, W.D.3
Kolich, C.H.4
Stahly, G.P.5
Fronczek, F.R.6
Watkins, S.R.7
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15
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77951023783
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note
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3N, and MeOH or t-BuOH), which led to numerous side products instead of rearrangement product 10a.
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16
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77951023448
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note
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Attempts to increase the rate of conversion to 10a by addition of catalytic HCl, and other more acidic alchohol solvents such as hexafluoroisopropanol and trifluoroethanol led in all cases to ester byproducts in addition to product 10a.
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23
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0037151592
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3 could also be responsible, see:
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3 could also be responsible, see:. Huang Y., and Rawal V.H. J. Am. Chem. Soc. 124 (2002) 9662-9663
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(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 9662-9663
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Huang, Y.1
Rawal, V.H.2
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24
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77951023808
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note
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Note that the majority of commercially purchased chloroform is stabilized with added ethanol, even if unspecified. Ethanol can compete with other alcohol nucleophiles to trap the isocyanate intermediate. We recommend using anhydrous chloroform stabilized with amylenes to avoid this complication.
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26
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77951023348
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Although acyl azides are a widely used intermediate in organic synthesis, the authors caution that low molecular weight acyl azides can be potentially explosive if evaporated to dryness. See: On larger scale, the authors recommend partial concentration of the acyl azide intermediate, followed by introduction of MeOH
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Although acyl azides are a widely used intermediate in organic synthesis, the authors caution that low molecular weight acyl azides can be potentially explosive if evaporated to dryness. See:. Overman L.E., Jessup P.J., Petty C.B., and Roos J. Org. Synth. 59 (1980) 1 On larger scale, the authors recommend partial concentration of the acyl azide intermediate, followed by introduction of MeOH
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(1980)
Org. Synth.
, vol.59
, pp. 1
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Overman, L.E.1
Jessup, P.J.2
Petty, C.B.3
Roos, J.4
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