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Synlett 1997; 1997(3): 231-240
DOI: 10.1055/s-1997-755
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Fenestranes in Recent Synthetic Developments

M. Thommen, Reinhart Keese*
  • *Institut für Organische Chemie, Universität Bern, Freiestrasse 3, 3012 Bern, Switzerland, Fax +41 31 631 3423; E-mail rk@ioc.unibe.ch
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Publication Date:
31 December 2000 (online)

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The systematic description of planarizing distortions of tetracoordinate carbon is outlined and specifically discussed for C(C)4 moieties which form the central part of fenestranes. Recent synthetic developments of the preparation of stereoisomeric [4.5.5.5]fenestranes and [5.5.5.5]fenestranes are described. Transformations with the aim of increased planarizing distortions are presented. The interaction of Fe2(CO)9 with a fenestradiene led to three structurally well defined Fe-carbonyl complexes.

Tandem-Pauson-Khan reaction - olefin-enone photocycloaddition - Pd(0) induced cyclization-carbonylation - high pressure Claisen-rearrangements - fenestradiene-Fe(CO)x complexes