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37049103557
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Similar problems and low yields have been, reported in the rearrangements of other 2-allyloxy N-heterocycles, such as tetrachloropyridines, quinolines, isoquinolines, benzoxazoles, benzthiazoles, and tetrazoles. See: (a) Iddon, B.; Hans, S.; Taylor, J. A. J. Chem. Soc., Perkin Trans. 1 1979, 2756-2761.
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Pd(O)-catalyzed rearrangement of E-crotyloxypyridine leads to a mixture of both, formal [1,3]- and [3,3]-sigmatropic rearranged products, whereas Pd(II) leads to clean [3,3]-rearrangement: Itami, K.; Yamazaki, D.; Yoshida, J. Org. Lett. 2003, 5, 2161-2164.
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85026850769
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For synthesis of COP-based Pd(II) catalysts, see: Anderson, C. E.; Kirsch, S. F.; Overman, L. E.; Richards, C. J.; Watson, M. P. Org. Synth. 2007, 84, 148-155.
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42
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74949108836
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See the Supporting Information for details
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See the Supporting Information for details.
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43
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74949087243
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Substrates 11a - e were prepared in a similar fashion to substrate 8 with conventional heating at 50 °C over 40 h instead of microwave heating
-
Substrates 11a - e were prepared in a similar fashion to substrate 8 with conventional heating at 50 °C over 40 h instead of microwave heating.
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44
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74949091439
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2-Allyloxypyrimidines have been reported to not undergo thermal rearrangement at 200 °C. See ref 8d
-
2-Allyloxypyrimidines have been reported to not undergo thermal rearrangement at 200 °C. See ref 8d.
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45
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0037458598
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Kang, J.; Kim, T. H.; Yew, K. H.; Lee, W. K. Tetrahedron: Asymmetry 2003, 14, 415-418.
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