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Synthesis of 2-acetoxy[5]helicene by sequential double aromatic oxy-Cope rearrangement

✍ Scribed by Yasushi Ogawa; Tetsuya Ueno; Michinori Karikomi; Katsura Seki; Kazuo Haga; Tadao Uyehara

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 80 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01611-8

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✦ Synopsis

Synthesis of 2-acetoxy[5]helicene has been achieved by sequential double aromatic oxy-Cope rearrangement strategy. Combination of 1-methoxybicyclo[2.2.2]oct-5-en-2-one and p-bromophenylmagnesium bromide gave 3-bromophenanthrene through several steps including an aromatic oxy-Cope rearrangement as a key step. The second oxy-Cope rearrangement and the following transformation gave 2-acetoxy[5]helicene by similar procedure.

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