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Unusual reactivity of highly strained cyclophanes

✍ Scribed by Friedrich Bickelhaupt; Willem H. de Wolf

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 403 KB
Volume: 11
Category: Article
ISSN: 0894-3230
DOI: 10.1002/(sici)1099-1395(199805)11:5<362::aid-poc34>3.0.co;2-f

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✦ Synopsis

An essential feature of the concept of aromaticity has been the stability and lack of reactivity of aromatics relative to that of other unsaturated compounds. Contrary to this general experience, high and unusual reactivity is encountered when simple, monocyclic benzene rings are bent by short bridges into a boat-shaped conformation, as is the case in small [n] paracyclophanes (n 8) and [n]metacyclophanes (n 7). This is illustrated, mostly with examples taken from the authors' own work, for thermal and photochemical behavior and reactions with electrophiles, nucleophiles and dienophiles.

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