in recrystallizing the picrate of 2,8-dimethyl-l,2,3,4-tetrahydroquinoline and filtrates from this recrystallization were yellow after standing for thirty days.)When the deep red filtrate from the. recrystallization of the picrate of 2,6-dimethyl-l,2,3,4-tetrahydroquinoline was allowed to stand for thirty days, orange crystals sepa-
Summary
Ozonolysis and chromatographic procedures as a method for determining the position of double bonds in olefinic acids are not entirely satisfactory. Ozonolysis is seriously limited because of the secondary reactions undergone by the ozonide. Chromatographic resolution of the decomposed ozonides of oleic acid yields the expected pelargonic and azelaic acids but also yields fractions that indicate double bonds which do not exist. Fractions corresponding to pimelic, sebacic, caprylic, suberic, and capric acids appeared. The “pimelic acid” fraction resulted from the reaction of ozone with an oxidizable or hydrolyzable solvent such as acetone, methanol, or tetrachloromethane. The “sebacic” and “caprylic acid” fractions were incompletely decomposed ozonide. The suberic and capric acid fractions however were real and are believed to have resulted from 8‐octadecenoic acid present in the oleic acid in amounts too small to be detected by the methods used to establish its purity.
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