Aconite Alkaloids. XIV.

On Hypognavin. (2)

Abstract

Dehydrogenation of hypognavinol with selenium was carried out and the neutral portion was purified by chromatography. The eluate was separated into the alkylnaphthalene and alkylphenanthrene fractions and crystalline alkylphenanthrene of m. p. 89-90.5° was obtained. This substance was found by mixed fusion and ultraviolet spectral data to be identical with the compound of m. p. 82-84° obtained by the selenium dehydrogenation of anhydroignavinol. Further a minute amount of crystalline alkylphenanthrene of m. p. 187-191° was obtained and was found to be 1, 8-dimethylphenanthrene by mixed fusion and comparison of ultraviolet spectra with the compound (m. p. 189-191°) obtained by synthesis. The third substance was an oily alkylphenanthrene giving a trinitrobenzene complex of m. p. 173-175° (decomp.), which was found by mixed fusion to be identical with the trinitrobenzene complex of m. p. 173-175° (decomp.) obtained similarly from anhydroignavinol. The chromatographic purification afforded basic substances forming a picrate of m. p. 272-275° (decomp.) and a perchiorate of m. p. 273-275° (decomp.). The volatile basic substance obtained was found to be ammonia which formed ammonium picrate of m. p. 285°(decomp.).