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Mechanism leading to the observed product of intramolecular aryl Diels–Alder reaction

✍ Scribed by Samuel Chackalamannil; Darı́o Doller; Keith Eagen

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
75 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

A mechanistic investigation into the recently reported intramolecular aryl Diels-Alder reaction was carried out using deuterium labeling. These studies led to the conclusion that the initial Diels-Alder adduct is isomerized to a highly conjugated tetra-ene intermediate which undergoes a stereospecific suprafacial 1,5-dienyl hydrogen shift to give the observed product.

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