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1. Novel ring-cleaving reaction of 4-nitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane with nucleophiles

Author

Merle A. Battiste, Wei Xu, Ion Ghiviriga, Will Wheelus, Florian Dulong, Efram Goldberg, Yian Zhai, and William R. Dolbier

Subjects
Chemistry, Cyanide, Aryl, Organic Chemistry, Ring (chemistry), Biochemistry, Medicinal chemistry, Inorganic Chemistry, chemistry.chemical_compound, Nucleophile, Nucleophilic substitution, Nitro, Environmental Chemistry, Physical and Theoretical Chemistry, Bond cleavage, Cyclophane
Abstract

When 4-nitro-AF4 is treated with nucleophiles such as alkoxides and cyanide, a novel ring opening, cyclophane destroying reaction is observed whereby, via an S N Ar mechanism, the nucleophile attacks the bridgehead aryl carbon vicinal to the nitro group with subsequent aryl-CF 2 bond cleavage.

Published
2008

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