Structural study of a kero base of formula C₁₆H₂₅N

The non-aromatic base, C₁₆H₂₅N, isolated from kerosene distillates by W. C. Thompson and J. R. Bailey has been further investigated. Conditions have been established for condensing the base with formaldehyde and, through oxidation of the condensation product, a dicarboxylic acid, C₁₄H₁₉N(COOH)₂, has been obtained. Step-wise decarboxylation of the acid has resulted in the production of a new monocarboxylic acid, C₁₄H₂₀N(COOH), and a new base, C₁₄H₂₁N. Proof of saturated behavior of the new base has established the presence of two methyl groups in the original base and has eliminated the possibility of acridine structure. Various structural possibilities for the C₁₆H₂₅N base have been discussed. The reaction of the base with cyanogen bromide has been investigated and additional evidence of the unusual structure of the compound has resulted from failure to effect ring cleavage by this reagent. Bromination of the base has been effected and the behavior of other naphthenic as well as aromatic kero bases under similar conditions has been studied. A possible application of bromination as a means of resolving mixtures of non-aromatic bases has been pointed out