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Contrasteric Diels-Alder reactions of 5-methyl-5-phenylcyclopentadiene |
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| Authors: | Masaru Ishida Makoto Itakura Hiroshi Tashiro |
| Institution: | Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan |
| Abstract: | The frontier molecular orbital of 5-phenylcyclopentadiene was predicted on the basis of the orbital mixing rule to deform to favor the Diels-Alder reaction in a syn contrasteric manner. The prediction was substantiated experimentally by the reactions of 5-methyl-5-phenylcyclopentadiene with dienophiles to afford the syn attack products, exclusively. |
| Keywords: | Cyclopentadienes Diels-Alder reactions Frontier molecular orbital Facial selectivities Substituent effects |
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