Novel ring-cleaving reaction of 4-nitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane with nucleophiles |
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| Authors: | William R Dolbier Jr Yian Zhai Wei Xu Will Wheelus Florian Dulong Efram Goldberg Ion Ghiviriga Merle A Battiste |
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| Institution: | Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, United States |
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| 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 SNAr mechanism, the nucleophile attacks the bridgehead aryl carbon vicinal to the nitro group with subsequent aryl-CF2 bond cleavage. |
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| Keywords: | [2 2]Paracyclophane AF4 Nucleophilic substitution Fluorine reactivity effects |
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