and 50 lb. of hydrogen pressure were used in each case. With ester II and platinum oxide catalyst, the reaction was complete in twenty minutes; with palladous oxide, the reaction required four hours. Ester III was reduced in two to four hours using platinum and, incompletely, after seven hours with palladium.The saturated ester (IV) was recovered upon fractionation of the alcoholic solution and identified by its boiling point, density and refractive index. 14 Degradation of High Boiling Ester (III).-Seven grams (0.05 mole) of the ester, boiling at 169°, was treated with 0.05 mole of hydrogen peroxide and 2 ml. of osmium tetroxide catalyst according to the procedure of Milas and Sussman.11 The gray solution was distilled under diminished pressure. The fraction boiling from 62 to 73 °contained the glycol (VII). This was treated with successive small portions of perchlorate -cerate ion in perchloric acid, "Ceric perchlorate,"12 (10 g. (NH4)2Ce(N03)6 in 50 ml. of 15 to 20% perchloric acid) until a red color ivas no longer formed. Air was blown through the warmed solution and then into a test-tube containing 2,4-dinitro-
butyl selenocyanate, although sealed in ampules and kept in the dark, turned black after a month; the yellow nhexyl compound slowly turned pink but got no darker; the colorless n-decyl compound remained colorless although exposed to light and air.
The iminochloritie was also obtained from 9-fluorylamine hydrochloride by the method of P e t e r~o n .~ Photochemical Decomposition of 9-Fluoryldichloramine.--\\;ithin a few hours of exposure t o sunlight of a solution of 11.8 g. of 9-fluoryldichloramine in 100 cc. of dry benzene contained in a stoppered Erlenmeyer flask, a white crystalline deposit settled on the wall of the flask. This behavior necessitated daily filtration and reexposure of the filtrate. In the course of a week 4.52 g. of 9-
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