Thommen, Marc; Prevot, Lionel; Eberle, Marcel K.; Bigler, Peter; Keese, Reinhart (2011). The quest for planarizing distortions in hydrocarbons: two stereoisomeric 4.5.5.5 fenestranes. Tetrahedron, 67(21), pp. 3868-3873. Kidlington, UK: Elsevier Science 10.1016/j.tet.2011.03.088
Full text not available from this repository. (Request a copy)According to semiempirical calculations the planarizing distortions in the central C(C)4 substructure of fenestranes, represented as 1, can be enhanced by a variety of structural modifications. Based on these results we selected the 7-hydroxy-c,c,c,c- and c,t,c,c[4.5.5.5]fenestranones 13 and 16 as precursors for the introduction of a bridgehead double bond. The efficient synthesis of these precursors and their chemical transformations are reported. Attempts to activate the hydroxyl group in 16 for introduction of a bridgehead double bond led to the rearrangement of the [4.5.5.5]fenestrane to a triquinacane skeleton. (C) 2011 Elsevier Ltd. All rights reserved.
Item Type: |
Journal Article (Original Article) |
|---|---|
Division/Institute: |
08 Faculty of Science > Other Institutions > Emeriti, Faculty of Science 08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Bigler, Peter, Keese, Reinhart |
ISSN: |
0040-4020 |
Publisher: |
Elsevier Science |
Language: |
English |
Submitter: |
Factscience Import |
Date Deposited: |
04 Oct 2013 14:27 |
Last Modified: |
05 Dec 2022 14:08 |
Publisher DOI: |
10.1016/j.tet.2011.03.088 |
Web of Science ID: |
000291072200011 |
URI: |
https://boris.unibe.ch/id/eprint/9773 (FactScience: 215552) |
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