Automerizations Thermal rearrangement of aromatic hydrocarbons

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subsequent work showed isomerization of azulene naphthalene not readily reversible ( free energy of naphthalene azulene isomerization high - approximately 90 kcal/mol). new reaction mechanism suggested involved carbene intermediate , consecutive 1,2-hydrogen , 1,2-carbon shifts across same c-c bond in opposite directions. preferred mechanism , follows:










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