Synthesis and base-induced epimerization of cis,cis,cis,trans-tribenzo[5.5.5.6]fenestranes

Authors
Bredenkotter, B Barth, D Kuck, D
Citation
B. Bredenkotter et al., Synthesis and base-induced epimerization of cis,cis,cis,trans-tribenzo[5.5.5.6]fenestranes, CHEM COMMUN, (9), 1999, pp. 847-848
Citations number
35
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
9
Year of publication
1999
Pages
847 - 848
Database
ISI
SICI code
1359-7345(19990507):9<847:SABEOC>2.0.ZU;2-8
Abstract
Strained cis,cis,cis,trans-tribenzo[5.5.5.6]fenestranes are accessible in g ood yield by two-fold cyclodehydration of cis-2,6-diphenylspiro [cyclohexan e- 1,2'-indane]-1', 3'-diols and the particularly high acidity of their 'in verted' benzylic bridgehead C-H bonds, causing facile epimerization to the more stable all-cis-tribenzo[5.5.5.6]fenestranes, is shown.