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- Title
Phenanthro-Annelated [5.5.6.6]- and (Broken) [6.5.6]Fenestranes.
- Authors
Bredenkötter, Björn; Neumann, Beate; Stammler, Hans‐Georg; Kuck, Dietmar
- Abstract
The construction of the polycyclic frameworks of phenanthro-annelated all- cis-[5.5.6.6]fenestrane, cis, cis, trans, cis-[5.5.6.6]fenestrane, and a related 'broken' [6.5.6]fenestrane is reported for the first time. On the basis of our established synthesis of benzoannelated fenestrindanes, spirocyclic di(9-phenanthryl)methyl-1,3-indanediols were prepared with complete stereocontrol and subjected to cyclodehydration. Surprisingly, the 9-phenanthrylmethyl residues underwent preferential ' peri' attack, rather than ' ortho' attack, to generate 1,10-phenanthro rather than 9,10-phenanthro units. In this way, the cyclodehydration of 2,2-di(9-phenanthryl)methyl-1,3-indanediol gives rise to two new six-membered rings with the [6.5.6]fenestrane skeleton. The cyclodehydration of the related trans- and cis-diphenanthryl spiro(cyclohexane-1,2′-indanediols) generated one new five- and one new six-membered ring stereospecifically to afford the respective all- cis- and cis, cis, trans, cis-benzodiphenanthro[5.5.6.6]fenestranes in good yields. The crucial constitutional and stereochemical features of the new fenestranes were determined by single-crystal X-ray structure analysis and variable-temperature (VT) NMR spectroscopy.
- Subjects
FENESTRANES; CYCLOHEXANE synthesis; ORGANIC synthesis research; NUCLEAR magnetic resonance spectroscopy; STEREOCHEMISTRY
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 1, p53
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301382