Reduction of aromatic hydrocarbons by lithium in ethylenediamine

Abstract

Various aromatic hydrocarbons, which can be assumed to represent some of the aromatic structures present in coals and chars, have been reduced under forcing conditions using lithium in ethylenediamine. It was found that: (i) Aromatic hydrocarbons highly substituted by alkyl or alicyclic groups are resistant to reduction. (ii) The less substituted benzene hydrocarbons and diphenyl-type structures yield, in addition to a proportion of fully reduced material, compounds containing a single olefinic bond which tends to resist further reduction.     (iii) Highly condensed hydrocarbons (such as pyrene or coronene) yield some perhydro derivatives, but a part of the product consists of less completely reduced compounds with aromatic and olefinic features; these compounds are more resistant to further reduction than the parent hydrocarbons.     (iv) Condensed polynuclear hydrocarbons yield also some products containing hydroxyl (phenolic) and carbonyl groups.