The unexpected effects of added ligands on the addition of phenyllithium to E-cinnamaldehyde in THF
The effect of donor ligands, usually expected to enhance the reactivity of organolithiums, was studied on the addition of PhLi to E-cinnamaldehyde in THF, under conditions that lead the reaction toward the production of 1,3-diphenylpropanone. It was observed that in the presence of TMEDA and HMPT, t...
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| Autores principales: | , |
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| Formato: | Artículo publishedVersion |
| Lenguaje: | Inglés |
| Publicado: |
2005
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p332_Vazquez |
| Aporte de: |
| Sumario: | The effect of donor ligands, usually expected to enhance the reactivity of organolithiums, was studied on the addition of PhLi to E-cinnamaldehyde in THF, under conditions that lead the reaction toward the production of 1,3-diphenylpropanone. It was observed that in the presence of TMEDA and HMPT, the rate of that reaction becomes slower than in the absence of ligands; the effect of HMPA was even more spectacular, at concentration [HMPA]: [PhLi] ≥ 4 the reaction becomes almost completely inhibited. These results show the complexity of solvation effects on the reactions of organolithiums and how substrate-reagent-ligand-solvent interactions are usually specific for the system under study. © ARKAT. |
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