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C→N Migrations of the ethoxycarbonyl group in reactions of ortho-substituted aryl isocyanates with the 1,3-zwitterion derived from triisopropylphosphine and ethyl 2-cyanoacrylate

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Abstract

The reactions of metapara-substituted aryl isocyanates with phosphorus-containing 1,3-zwitterions, which proceed with the C→N migration of the CO2Et group to form the corresponding carbamates, were extended to ortho-substituted aryl isocyanates. The influence of the steric and electronic effects of the ortho substituents in the aromatic rings of aryl isocyanates on the ease of this rearrangement is qualitatively considered.

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Gololobov, Y.G., Petrovskii, P.V., Ivanova, E.M. et al. C→N Migrations of the ethoxycarbonyl group in reactions of ortho-substituted aryl isocyanates with the 1,3-zwitterion derived from triisopropylphosphine and ethyl 2-cyanoacrylate. Russian Chemical Bulletin 52, 427–436 (2003). https://doi.org/10.1023/A:1023427403905

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  • DOI: https://doi.org/10.1023/A:1023427403905

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