The thermally mediated rearrangement of the polar aromatic, azulene, to the nonpolar benzenoid, naphthalene, has interested both experimentalists and theoreticians for decades. Several groups have attempted to elucidate the mechanism of this rearrangement but questions still remain as to its exact pathway. The currently accepted view is that two radical promoted mechanisms, the spiran mechanism and the methylene walk mechanism, both play an important role.  However, previous research using muon spin spectroscopy has suggested that the addition of a methylene or a hydrogen radical to a bridge head carbon, which both mechanisms invoke, is highly unfavorable. To investigate this problem, muonium (Mu = �+e-), a light �isotope� of hydrogen, was used to probe azulene.  We have detected and identified the radical products of the addition of Mu to azulene, based on comparison of the hyperfine coupling constants of the spin active species with the aid of computational predictions.

Computational and experimental muon spin spectroscopy studies of the thermally mediated rearrangement of azulene into napthalene

244th National Meeting (2012)

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