Abstract
Diphenyliodonium tetrafluoroborate and diphenyliodonium hexafluorophosphate have been found to generate up to two equivalents of hydrogen fluoride per equivalent of the iodonium salt by pyrolysis at 239°C in the neat state and at 150°C in the presence of anisole or nitrobenzene. The formation of hydrogen fluoride is presumed to arise by dissociation of hydrogen tetrafluoroborate or hydrogen hexafluorophosphate initially formed, due to the high temperatures, thus giving rise also to the Lewis acids boron trifluoride and phosphorus pentafluoride, respectively. A detailed analysis of the volatile organic products of the decomposition of the diphenyliodonium salts was also carried out. Many products were identified in all of the cases studied. For example, the neat decomposition of diphenyliodonium tetrafluoroborate afforded benzene, fluorobenzene, iodobenzene, the three isomeric iodobiphenyls, biphenyl, three isomeric terphenyls, and one or more of the diiodobiphenyls, iodoterphenyls, and polyaromatics. Among the iodobiphenyls, the ortho and para isomers were found to predominate over the meta isomer. The terphenyl isomers did not exhibit this ortho, para selectivity. It was significant that decomposition of the diaryliodonium salts in anisole suspension did not afford methoxybiphenyls or iodomethoxybiphenyls. An interpretation of these results is presented. © 1996 John Wiley & Sons, Inc.
Published Version
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