Density functional theory studies on the mechanisms of regioselective allylic and cis-vinylic deprotonation of allyl amides and allylamines |
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Authors: | Haeffner Fredrik Jacobson Madeleine A Keresztes Ivan Williard Paul G |
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Institution: | Department of Chemistry, Brown University, Providence, RI 02912, USA. fredrick_haeffner@brown.edu |
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Abstract: | A density functional theory (B3LYP/6-31+G) study was undertaken in an effort to learn more about the mechanisms controlling the regioselective deprotonations of the synthetically versatile N-lithio-N-(tert-butyl)allylamide 1 and N-lithio-N-(trimethylsilyl)allylamine 2 compounds. The calculations suggest that deprotonation of 1 occurs exclusively at the allylic position. This agrees with experimental results. The calculations also suggest that deprotonation of allylamine 2 exclusively at the cis-vinylic position is due to kinetic control. |
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