Stereoelectronic Effects on Dienophile Separation Influence the Diels-Alder Synthesis of Molecular Clefts
| Autor: | Jeffrey Y. W. Mak, David P. Fairlie, Allan H. White, Martin J. Stoermer, Alexandre N. Sobolev, David C. R. Hockless, Karl A. Byriel, Brian W. Skelton, W. A. Wickramasinghe |
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| Rok vydání: | 2017 |
| Předmět: |
Cyclopentadiene
Diene 010405 organic chemistry Stereochemistry Organic Chemistry 010402 general chemistry 01 natural sciences Cycloaddition 0104 chemical sciences Adduct chemistry.chemical_compound chemistry Diels alder Pi interaction Reactivity (chemistry) Physical and Theoretical Chemistry Structural rigidity |
| Zdroj: | European Journal of Organic Chemistry. 2017:6793-6796 |
| ISSN: | 1434-193X |
| Popis: | The formal cycloaddition adduct of 1,4-benzoquinone with two equivalents of cyclopentadiene is a scaffold with two non-conjugated alkenes. Both alkenes undergo endo [4+2] cycloaddition with a diene to form a rigid U-shaped molecular cleft. Here we show experimental, computational and structural evidence that π interactions between the alkenes affect structural rigidity, Diels–Alder reactivity, cleft formation and host–guest capture. |
| Databáze: | OpenAIRE |
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