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Synlett 1996; 1996(4): 385-386
DOI: 10.1055/s-1996-5414
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Access to the Bicyclo[5.3.1]undecadiene Ring System by Two Carbon Ring Enlargement of Bicyclo[3.3.1]nonane Derivatives

Michel Miesch* , Gaëtan Mislin, Michel Franck-Neumann
  • *Laboratoire de Chimie Organique Synthétique, associé au CNRS, Institut de Chimie, Université Louis Pasteur, 1 rue Blaise Pascal, 67000 - Strasbourg (France), Fax: (33).88.60.42.48, E-mail: mfneu@chimie.u-strasbg.fr
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Publication History

Publication Date:
31 December 2000 (online)

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Several electrophilic cyclobutenes were synthesized by non photochemical methods to test the possibility of using them for the transformation of the tricyclo[5.3.1.02,5]undecene system into the bicyclo[5.3.1]undecadiene system. The electrophilic cyclobutenes obtained from the reaction of a bicyclo[3.3.1]nonane enamine (or silyl enol ether) with acetylenic esters failed to give a ring enlargement. However a direct 2-carbon ring enlargement was observed starting from the enolate of a bicyclo[3.3.1]nonane β-ketoester and esters of acetylenic acids.

Enamine - silyl enol ether - β-ketoester enolate - zirconium tetrachloride - [2+2] cycloaddition