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EnglishEndo–exo Selectivity in Diels–Alder cycloadditions of several o-quinodimethanes (1–4) with acrylonitrile, 2-(5H)-furanone and N-methylmaleimide has been investigated in acetonitrile solution. Theoretical data reproduce fairly well both experimental absolute reaction rates and diastereoisomer ratios. The high endo selectivity has been rationalized mainly as a result of solvation effects (acetonitrile, PCM model) and reactant deformations. The latter is due to steric interactions.
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| Titolo: | Reactivity and Diastereoselectivity in the Diels-Alder Reaction of o-Quinodimethanes. An Experimental and DFT Computational Study |
| Autori: | |
| Data di pubblicazione: | 2000 |
| Rivista: | |
| Abstract: | Endo–exo Selectivity in Diels–Alder cycloadditions of several o-quinodimethanes (1–4) with acrylonitrile, 2-(5H)-furanone and N-methylmaleimide has been investigated in acetonitrile solution. Theoretical data reproduce fairly well both experimental absolute reaction rates and diastereoisomer ratios. The high endo selectivity has been rationalized mainly as a result of solvation effects (acetonitrile, PCM model) and reactant deformations. The latter is due to steric interactions. |
| Handle: | http://hdl.handle.net/11571/108052 |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
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