The reaction of iodine monochloride with polycyclic aromatic compounds: polar and electron transfer pathways

…, RF O'Malley, DJ Sardella, LS Barinelli…

Index: Turner, Dean E.; O'Malley, Robert F.; Sardella, Dennis J.; Barinelli, Lucio S.; Kaul, Pushkar Journal of Organic Chemistry, 1994 , vol. 59, # 24 p. 7335 - 7340

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Citation Number: 37

Abstract

Several polycyclic aromatic hydrocarbons were treated with iodine monochloride. Although iodination is the predominant reaction of benzenoid arenes, chlorination is the sole reaction with anthracene, phenanthrene and naphthalene compounds (except for 5), whose oxidation half-wave potentials are less than 1.58 V vs Ag/Ag+(0.1 M). Arenes with higher potentials are unreactive. Naphthalene (9) and its derivatives with mild electron- ...