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Diepoxy[18]annulene(10.0) : (Z,E,Z,E,Z)-Diepoxy[18]annulen(10.0) – ein hochdynamisches Annulen

✍ Scribed by Gottfried Märkl; Thomas Knott; Peter Kreitmeier; Thomas Burgemeister; Fritz Kastner

Publisher
John Wiley and Sons
Year
2000
Tongue
German
Weight
213 KB
Volume
83
Category
Article
ISSN
0018-019X

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✦ Synopsis

Diepoxy [18]annulenes(10.0): (Z,E,Z,E,Z)-Diepoxy [18]annulene(10.0) ± a Highly Dynamic Annulene

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 (Z,E,E,Z,E)-configured. The 1 H-NMR data confirm that in 6 the (E)-ethene-1,2diyl bonds (C(11)C( 12) and C( 15)C( 16)) rotate around the adjacent s-bonds. Beginning at À 708, 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.

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