Dehydroamination of 9-alkylamino-9,10-dihydrophenanthrene occurred at 190—250 °C under non-basic conditions to give phenanthrene exclusively. The thermal reaction of cis-9-t-butylamino-10-methoxy-9,10-dihydrophenanthrene gave both 9-methoxyphenanthrene and 9-t-butylaminophenanthrene, while 9-aminophenanthrene was obtained from the thermal reaction of 9-amino-10-methoxy-9,10-dihydrophenanthrene. The thermal reaction of 9-amino-9,10-dihydroanthracene gave both anthracene and 9-aminoanthracene. Analysis of activation energies and frequency factors showed that the dehydroamination proceeds via an intramolecular proton transfer from C-10 to the amino group and subsequent C–N bond cleavage.
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