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Cyclophanes, XXXIX. The Structure of the Dicyanoacetylene Adducts of [2.2]Paracyclophane

✍ Scribed by Hopf, Henning ;Witulski, Bernhard ;Jones, Peter G. ;Schomburg, Dietmar

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 393 KB
Volume: 1995
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199519950484

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✦ Synopsis

Cyclophanes / Diels-Alder reactions / Cyanoacetylenes / [2 +4] Cycloadditions / Barrelenophanes / Semibullvalenophanes

The structures of the 1 : 1 and 1 : 2 addition products of dicyanoacetylene (2) to [2.2]paracyclophane (I) have been determined by X-ray structural analysis as 3 and 5, respectively. In contrast to literature reports, the latter possesses the "cros-sed" double barrelene configuration. On irradiation 3 isomerizes to the semibullvalenophane 4 as was also shown by Xray structural analysis.

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