Dibenzothiophene chemistry, reductive

Dibenzothiophene Chemistry. Unlike with perylene and deca-cylene, for which reductive alkylation leads simply to the addition of alkyl groups to aromatic compounds, the reductive alkylation of dibenzothiophene can lead to biphenyl (8). This product occurs by the loss of sulfur from dibenzothiophene, followed by the uptake of two protons. Using reaction times of 1-4 h at room temperature, one can isolate a 2-biphenylyl, alkyl sulfide this finding indicates that the anion on sulfur can have some stability. We investigated this situation by performing 2H NMR on a product of the reaction of CD3I with a dibenzothiophene anion solution formed by adding 2 mol of K per mole of dibenzothiophene. 

PERYLENE REDUCTION IN THE PRESENCE OF NAPHTHALENE. The chemistry that we have discussed is similar to that of Sternberg and co-workers (1, 2) in using an excess of potassium metal in THF at room temperature. In the Sternberg and co-workers approach, however, naphthalene was used to transfer electrons from potassium metal to the substrate under investigation whether it was a fossil fuel, such as coal (2), or a model compound, such as dibenzothiophene (8). Thus, the results of our work on the direct reduction of perylene by K° might differ from results of a reaction in which naphthalene is present. 

---