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Regioselective radical ring-opening reaction of bicyclo[4.2.0]octan-2-ones promoted by samarium(II) iodide

✍ Scribed by Kiyomi Kakiuchi; Koichi Minato; Ken Tsutsumi; Tsumoru Morimoto; Hideo Kurosawa

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 261 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00085-6

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✦ Synopsis

Radical ring-opening reactions of bicyclo[4.2.0]octanones, its C6 alkyl derivatives, and tricyclic ketones promoted by SmI 2 gave cyclohexanones via fission of the external cyclobutane bond. The CO 2 Me, CN, and phenyl derivatives led to the production of the eight-membered ring compounds through cleavage of the central cyclobutane bond. Using this regioselective reaction, the synthesis of (±)-acorenone was achieved.

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