Markl, G and Knott, T and Kreitmeier, P and Burgemeister, T and Kastner, T (2000) Diepoxy[18]annulenes(10.0): (Z,E,Z,E,Z)-diepoxy[18]annulene(10.0) - a highly dynamic annulene. HELVETICA CHIMICA ACTA, 83 (3). pp. 592-602. ISSN 0018-019X,
Full text not available from this repository.Abstract
The McMurry reaction of (all-E)-5,5'-([2,2'-bifuran]5,5'-diyl)bis[penta-2,4-dienal] (13) only occurs intramolecularly to give a mixture of the diepoxy[18]annulenes(10.0) 6 and 7. Tetraepoxy[36]annulene(10.0.10.0) resulting from an intermolecular McMurry reaction is not formed. According to spectroscopic data, 6 is (Z,E,Z,E,Z)- and 7 (ZE,E,Z,E)-configured. The H-1-NMR data confirm that in 6 the (E)-ethene-1,2-diyl bonds (C(11)=C(12) and C(15)=C(16)) rotate around the adjacent sigma-bonds Beginning at -70 degrees, this rotation freezes, and 6 is becoming a diatropic aromatic ring system. Beside [18]annulene itself, (Z,E,Z,E,Z)-diepoxy[18]annulene(10.0) 6 is the only hitherto known [18]annulene derivative with dynamic properties.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 17 May 2021 14:34 |
| Last Modified: | 17 May 2021 14:42 |
| URI: | https://pred.uni-regensburg.de/id/eprint/42959 |
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