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Intramolecular [8+2] cycloaddition and 10π-electron electrocyclization reactions of an 8-acylheptafulvene

✍ Scribed by Ching-Yang Liu; K.N Houk

Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 167 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)95928-8

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✦ Synopsis

heptafulvene, 8, undergoes both an intramolecular [8+21 cycloaddition and a loll-electron electrocyclization followed by 1,5-sigmatropic hydrogen shifts to give 10 and 12, respectively.

Acetylheptafulvene, 1, was reported to be unstable by Hafner,' although the reaction of 1 with DMAD to give an intermolecular C8+21 cycloadduct was observed. Bertelli s & reported that attempted preparation of 1 or 3 led to rearrangement or cyclization, as shown below, but gave no isolable acetylheptafulvene derivatives.*

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