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

Synthesis and modification of octafluoro[2.2]paracyclophane (parylene AF4)

“…29 An unusual reaction product of nucleophilic attack of the nitro analogue 31 led to the discovery of a novel ring cleaving reaction of fluorinated cyclophanes (Scheme 17). 30 Although Scheme 12 The preparation of trifluoromethyl substituted bis AF4 analogues.…”

Reaction mechanisms : Part (iii) Polar reactions

“…The nucleophile attacks at the bridgehead aryl carbon vicinal to the nitro group with subsequent aryl-CF 2 bond cleavage to give 138. 75 measured and was used to unusually high polarity of the mixed solvent. In pure chloroform the hydrogen bond donor 145 is poorly solvated and in pure tetrahydrofuran the hydrogen bond acceptor 144 is poorly solvated however in the mixed solvent each interact strongly with the solvent which they select from the mixture.…”

Discrimination of pseudo‐meta and pseudo‐para diamino‐octafluoro[2.2]paracyclophanes by 1H, 19F, and 13C NMR

“…The spectroscopy of these compounds is particularly interesting, and nuclear magnetic resonance (NMR) is no exception . With the advancements in syntheses of bridge‐fluorinated [2.2] paracyclophanes, and their potential utility as monomers in high‐performance polymers, the spectroscopy of this class of compounds has been an area of particular interest. The presence of fluorine atoms in this class of cyclophanes render these compounds amenable to study by 19 F NMR, which is highly sensitive and intrinsically information‐rich, and provides unique insight into their chemistry.…”