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Contrasteric Diels–Alder reactions of 5-methyl-5-phenylcyclopentadiene

✍ Scribed by Masaru Ishida; Makoto Itakura; Hiroshi Tashiro

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
436 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

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-5phenylcyclopentadiene with dienophiles to afford the syn attack products, exclusively.

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