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Article Dans Une Revue Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases Année : 2013

Substituent Effects in Ugi–Smiles Reactions

Résumé

In a recent communication, we described the mechanism of the well-known Ugi-type reactions with a model system ( J. Org. Chem. 2012, 77, 1361−1366). Herein, focusing on the Ugi–Smiles coupling, we study the effects of each of the four reactants on the energy profile to further explain the experimental results. The variations observed with different carbonyl compounds rely on their influence on the formation of the aryl-imidate, whereas the variations on the amine preferentially affect the Smiles rearrangement. The effect of substituents on the phenol derivative is seen upon both aryl-imidate formation and the rearrangement. The effect of the isocyanide substituents is less pronounced.
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Dates et versions

hal-01116243 , version 1 (12-02-2015)

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Nicolas Chéron, Romain Ramozzi, Laurent El Kaim, Laurence Grimaud, Paul Fleurat-Lessard. Substituent Effects in Ugi–Smiles Reactions. Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, 2013, 117 (33), pp.8035-8042. ⟨10.1021/jp4052227⟩. ⟨hal-01116243⟩
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