9-Aminophenanthrene (1) gave an aminophenanthrene sulfonic acid (3) almost free from the isomers upon baking its bisulfate under various conditions. An excellent yield (98%) was attained when the reaction was carried out at 220°C under 4 mmHg. The structure of (3) was determined to be 9-aminophenanthrene-3- sulfonic acid based on the facts that (3) was synthesized by ammonolysis of 9-bromophenanthrene -3-sulfonic acid (2) and that (2) was derived by the Sandmeyer reaction from (3). Direct sulfonation of (1) with concentrated sulfuric acid proceeded with great ease and gave a mixed product of monosulf onic acids and polysulf onic acids even when the reaction was conducted at a low temperature so as to retain the major portion of the (1) unreacted. Trials to separate the mixture into its components failed to succeed.

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A series of aliphatic-aromatic polyureas were prepared from α, ω-bis [p-(-aminopropyl) phenoxy] alkanes and bis [p-(-aminopropyl) phenoxy] ω, ω'-dialkyl ethers upon treatment with diphenyl carbonate. The diamines such as bis [p-(-aminopropyl) phenoxy]-1, 2-ethane, -1, 3-propane, -1, 4-butane, -1, 5-pentane, and -1, 6-hexane were obtained by the reduction of the corresponding dinitriles. The desired dinitriles were synthesized from β-(p-hydroxyphenyl) propionitrile and α, ω-dihalogenoalkanes. Bis p-(-aminopropyl) phenoxyj-a, a'-dimethyl ether and -β, β'-diethyl ether were similarly synthesized from, β-(p-hydroxyphenyl) pro-pionitrile and ω, ω'-dihalogenoalkyl ethers. The polyureas obtained under the equimolar conditions were fusible and soluble polymers. They are crystalline in all cases and have crystalline melt temperatures in the range of 179 to 269°C. When some excess of diphenyl carbonate was added -to the reaction mixture, the polymers obtained became infusible and insoluble. The reaction mechanism of diamine with diphenyl carbonate has been discussed.

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In order to effect selective hydrogenation of α, β-unsaturated carbonyl compounds into unsaturated alcohols, the preparative methods of Raney type catalysts and the reaction conditions have been studied. The catalysts were prepared by leaching various Raney alloys in aqueous alkaline solutions containing a small amount of metal salts. The best results were obtained when a Raney-copper alloy and cadmium nitrate were used. In the presence of this catalyst, crotonaldehyde was converted to crotyl alcohol in a yield above 80%. Hydrogenation of other α, β-unsaturated compounds was also carried out and their reactivities were compared.

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A new reaction to synthesize 3, 5-substituted-2-oxazolidone from .N-phenylurethane and phenyl glycidyl ether has previously been discovered by the authors. In the present study, this reaction was applied to the reactions between N-arylurethanes and aryl glycidyl ethers. Twelve types of urethanes and 9 types of glycidyl ethers were synthesized and used for the study in various combinations. In all cases, 3-aryl-5-aryloxymethyl-2-oxazolidones were formed with no difficulty. Versatility of the reaction has thus been established. The synthetic procedures and the properties of the oxazolidone derivatives are described in detail.

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The reactions of lead tetraacetate with alkylaromatic compounds, acetophenone, halobenzenes, biphenyl, and anisole have been investigated. Controlled lead tetraacetate oxidation of alkylaromatic compounds offers a new method for the synthesis of substituted benzyl acetates. Acetophenone reacted at 120°C to give phenacyl acetate and phenacylidene acetate, the former being higher in yield. But neither nuclear acetoxylated nor nuclear methylated products were detected. Both chloro-benzene and bromobenzene gave nuclear acetoxylated products, the isomer distributions being, for chlorobenzene : o-, 85; m-, 5; p-, 10; and for bromobenzene: o-, 54; m-, 16; p-, 30%. Biphenyl reacted only at the reflux temperature to give acetoxybiphenyl. Anisole gave guaiacol acetate at 120°C, neither the m- and p-isomers nor the methylated products being detected.

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