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Formal [6+4] cycloaddition of a dicobalt acetylene complex with furan derivatives

✍ Scribed by Koichiro Dota; Tadashi Shimizu; Shoji Hasegawa; Masaaki Miyashita; Keiji Tanino

Book ID: 104098765
Publisher: Elsevier Science
Year: 2011
Tongue: French
Weight: 725 KB
Volume: 52
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.12.063

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✦ Synopsis

An efficient method for constructing a 10-membered carbocycle with an oxygen bridge has been developed on the basis of a formal [6+4] cycloaddition reaction. Under the influence of EtAlCl 2 , a dicobalt hexacarbonyl acetylene complex possessing a benzoyloxy group and an allylsilane moiety reacted with furan to give a 11-oxabicyclo[6.2.1]undec-9-ene derivative. On treatment with iodine, the cycloadduct underwent decomplexation followed by rearrangement of the oxygen bridge to afford a 11-oxabicyclo[5.3.1]undeca-1,5-diene derivative.

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