Electrolyte Catalysis in the Ammonolysis of 9-Phenyl-9-chlorofluorene by Liquid Ammonia¹

Abstract

The ether which had been removed by distillation was found to contain acetone, identified by conversion to dibenzalacetone, m. p. 111.5-112.5°, both alone and when mixed with an authentic sample.Oxidation of Saturated Ketones to Acids: (1) Methyl re-Amyl Ketone Condensation.-Five-hundredths mole of 2-methyl-5-decanone was oxidized with 0.15 mole of sodium dichromate, 0.6 mole of sulfuric acid and 250 ml. of water as previously described.2a•16 Considerable carbon dioxide was evolved at the start and throughout the course of the oxidation. A total of 0.09 mole of acid was obtained. re-Caproic acid was identified in the waterinsoluble acid fraction by conversion to the 2-alkyl benzimidazole,17 m. p. 157-158°, which showed no depression when mixed with the known re-caproic acid derivative, m. p. 158-158.5°. Acetic acid was shown to be present in the water-soluble fraction by preparing the £-toluide, m. p. 146.5-147.5°, alone and when mixed with known acetop-toluide.(2) Methyl re-Hexyl Ketone Condensation.-Five-hundredths mole of 2-methyl-5-undecanone, oxidized as above, gave 1.1 moles of total acids. re-Heptoic acid was identified in the water-insoluble fraction by conversion to the piperazonium salt,18 m. p. 97-98°, which showed no depression when mixed with authentic piperazonium di-ro-heptoate, m. p. 96-97 °. Isovaleric acid was also shown to be present by preparing the piperazonium salt, m. p. 140-141°, alone