Automerization is the name given to a process in which carbon-ring chemicals tend to spontaneously transform into closely-related chemicals when heated.
The first example found was the transformation of azulene to naphthalene.
The 'reactions' involve a re-arrangement (so called 'scrambling') of the atoms in the chemicals' carbon ring.
[…] since the characterization of the automerization of naphthalene by Scott in 1977, similar atom scramblings of other aromatic hydrocarbons such as pyrene, azulene, benz[a]anthracene and even benzene have been described. While the existence of these reactions has been confirmed, the isomerization and automerization mechanisms remain unknown.
Note: Various mechanisms have been proposed to explain the changes - some at quantum level, e.g. 'carbon tunnelling' - but none has been formally adopted.
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