Hexafluorophosphate of the Bis(naphthalene) Radical Cation

Comparison of Polynuclear Aromatic Hydrocarbon Cation Salts with Salts of Simple Fluoroaromatic Cations

“…While polymerization is never (S) observed in the AsFS reaction, some of the diphenylarsonium salt is always formed in the 02+ and C6F6+ reactions due to the presence in the reaction mixture of arsenic pentafluoride formed in the decomposition of the oxidizing agents. This suggests that the first step toward polymerization is electron oxidation of C6~ (I = 212 kcal mol-1 ) to C6~+' and that AsFS is not able to achieve this oxidation: (6) 10 Subsequent abstraction of g+ by the anion may also occur: (7) Such interpretations are consistent with the conclusions of other investigators as to the cationic nature of intermediates in the preparation of poly(paraphenylene). (11,12,13) …”

Metal‐ and Chemical‐Oxidant‐Free CH/CH Cross‐Coupling of Aromatic Compounds: The Use of Radical‐Cation Pools

“…The desired cross‐coupling product 4 was obtained in 33 % yield (Table 1, entry 2). Four moles of 2 is necessary to produce one mole of 4 because 3 is accumulated as a complex with 2 (the radical cation of the naphthalene dimer)13a and 4 is produced by the reaction of 1 and 3 followed by one‐electron oxidation, wherein the radical‐cation naphthalene dimer is the oxidant.…”

Electrogenerated Cationic Reactive Intermediates: The Pool Method and Further Advances

“…Schubert and co-workers reported that the electrochemical oxidation of naphthalene in Bu 4 NPF 6 /CH 2 Cl 2 at −45 °C in an undivided cell afforded red-violet needles with an approximate composition of (C 10 H 8 ) 2 PF 6 . X-ray analysis of the compound revealed that two naphthalene molecules interact with each other and that the distance between the two naphthalene planes is 320 pm, indicating the stabilization of the radical cation of naphthalene by neutral naphthalene.…”