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Thermal reaction between acrylamides and alkyl azides at room temperature could afford triazolines but not aziridines in the absence of TfOH. See:
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Thermal reaction between acrylamides and alkyl azides at room temperature could afford triazolines but not aziridines in the absence of TfOH. See:. Yang C.-H., Shen H.-J., Wang R.-H., and Wang J.-C. J. Chin. Chem. Soc. 49 (2002) 95
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The aziridine products (at fairly low yields) from methyl acrylate and acrylonitrile may not come from the TfOH-promoted pathway. They may be generated from the thermal [3+2] cycloaddition between the azide and the olefin followed by nitrogen extrusion. See Ref. 7 for more information.
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Noteworthy, Aube et al. recently reported that Lewis acids activate the reaction between enones and azide derivatives along a domino reaction path, the first step corresponds to a [3+2] cycloaddition to afford 1,2,3-triazolines, followed by a ring contraction process to obtain the final enaminone product. See:
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Noteworthy, Aube et al. recently reported that Lewis acids activate the reaction between enones and azide derivatives along a domino reaction path, the first step corresponds to a [3+2] cycloaddition to afford 1,2,3-triazolines, followed by a ring contraction process to obtain the final enaminone product. See:
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