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‘Oligomere' Kondensationsprodukte von (1E,3E,5E)-1,6-Di(2-furyl)hexa-1,3,5-trien mit Acetaldehyd: Tetrahydro-tetramethyl-octaepoxy[60]annulen(6.1.6.1.6.1.6.1)

✍ Scribed by Gottfried Märkl; Robert Ehrl; Peter Kreitmeier

Book ID: 102254185
Publisher: John Wiley and Sons
Year: 2003
Tongue: German
Weight: 144 KB
Volume: 86
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200390076

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✦ Synopsis

Abstract

Oligomeric Condensation Products of (1**E,3E,5E****)‐1,6‐Di(2‐furyl)hexa‐1,3,5‐triene with Acetaldehyde: Tetrahydro‐tetramethyl‐octaepoxy[60]annulene(6.1.6.1.6.1.6.1)**

The Ca(NO~3~)~2~‐induced condensation of (1__E__,3__E__,5__E__)‐1,6‐di(2‐furyl)hexa‐1,3,5‐triene (6) with acetaldehyde yields the linear ‘oligomers' 7–11 with 2–6 1,6‐di(2‐furyl)hexa‐1,3,5‐triene units and 1–4 acetaldehyde units, besides a cyclic condensation product 12 obtained from 4 equiv. of 6 with 4 equiv. of acetaldehyde. According to spectroscopic studies, 12 is the tetrahydro‐tetramethyl‐octaepoxy[60]annulene(6.1.6.1.6.1.6.1) as the most expanded annulene system known so far. While the dehydrogenation of 12 to give the tetramethyl‐octaepoxy[60]annulene(6.1.6.1.6.1.6.1) cannot be achieved, the oxidation of 12 with Br~2~ yields a black, in all organic solvents nearly insoluble solid 14, which possibly is the tetramethyl‐octaepoxy[58]annulene(6.1.6.1.6.1.6.1) dication. Because of the insolubility of 14, unfortunately most of its spectroscopic data are not available. However, the λ~max~ values in the UV/VIS/NIR spectrum of 14 (Soret and Q bands) are in line with the values of the tetraepoxy[26]annulene(4.2.4.2) dication, the tetraepoxy[30]annulene(4.4.4.4) dication, and the tetraepoxy[34]annulene(6.4.6.4) dication.

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