Abstract
Benzene mixed with hydrogen fluoride and a platinum or rhodium catalyst is hydrogenated at room temperature and 1–5 atm pressure to yield cyclohexane and a reductive coupling product, phenylcyclohexane, the latter amounting to as much as 25% by weight of the hydrogenation products. Similarly, reductive coupling products are obtained from phenol or chlorobenzene, the former giving cyclohexylidine diphenol and the latter a mixture of monochlorinated phenylcyclohexanes. Results are consistent with the assumption that these reactions proceed by way of cycloalkene intermediates which react with unchanged aromatic compound to form the reductively coupled products. Readily available equipment for such hydrogenations is described.
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