Formation of epoxides and N-arylaziridines via a simple Mg-Barbier reaction in DMF
The Mg-activation of benzal bromide 2b in DMF in the presence of carbonyl compounds 1 or imines 4 leads to epoxides 3 and N-arylaziridines 5, respectively, with acceptable isolated yields. It was found that DMF is likely involved in this process to form a nucleophilic intermediate by reaction with a...
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| Veröffentlicht in: | Tetrahedron 2014-01, Vol.70 (4), p.919-923 |
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| container_title | Tetrahedron |
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| creator | Oudeyer, Sylvain Léonel, Eric Paugam, Jean Paul Nédélec, Jean-Yves |
| description | The Mg-activation of benzal bromide 2b in DMF in the presence of carbonyl compounds 1 or imines 4 leads to epoxides 3 and N-arylaziridines 5, respectively, with acceptable isolated yields. It was found that DMF is likely involved in this process to form a nucleophilic intermediate by reaction with a first generated electrophilic carbene. Results obtained in this chemical approach are compared to those obtained using electrochemical activation, also in DMF.
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| doi_str_mv | 10.1016/j.tet.2013.12.016 |
| format | Article |
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| ispartof | Tetrahedron, 2014-01, Vol.70 (4), p.919-923 |
| issn | 0040-4020 1464-5416 |
| language | eng |
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| source | Elsevier ScienceDirect Journals Complete |
| subjects | Acceptability Benzal halides Carbenes Carbonyl compounds Carbonyls Electrochemical activation Formations Imines Magnesium Mg-Barbier reaction Small ring cycles Tetrahedrons |
| title | Formation of epoxides and N-arylaziridines via a simple Mg-Barbier reaction in DMF |
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