Electrophilic Substitution of Hydrogen in Betulin and Diacetylbetulin |
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Authors: | I V Bodrikov Yu A Kurskii A A Chiyanov A Yu Subbotin |
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Institution: | 1.Alekseev Nizhny Novgorod State Technical University,Nizhny Novgorod,Russia;2.Razuvaev Institute of Organometallic Chemistry,Russian Academy of Sciences,Nizhny Novgorod,Russia;3.Lobachevsky State University of Nizhny Novgorod,Nizhny Novgorod,Russia |
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Abstract: | Betulin and diacetylbetulin, which can be regarded as sterically hindered alkenes, reacted with N-chloro-, N-bromo-, and N-iodosuccinimides to give products of allylic and vinylic substitution in quantitative overall yield. The contribution of allylic substitution increases in the series Cl < Br < I. Quantum chemical simulation of the reactions of diacetylbetulin with N-halosuccinimides showed that, regardless of the electrophile power, all reactions involve open-chain carbocationic intermediates. The direction of deprotonation of the latter with formation of allylic or vinylic substitution products is determined by preferential orientation of the vacant orbital and C–Hlg bond. |
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