Reactions of Hydrogen Azide with Alicyclic Alcohols 3287 decomposed at 290-295°; recrystallized from ethanolwater, it decomposed at 295°. Both samples burned in a flame leaving a grayish residue which when moistened with distilled water tested alkaline to litmus. Both samples and acetylacetone gave the same derivatives with 2,4-dinitrophenylhydrazine, melting at 122°( lit.122°).13Crude Yr melted at 38-40°, recrystallized from low boiling Skellysolve, m.p. 43°( lit. 43°6). After boiling with water, it gave the derivative of acetylacetone with 2,4-dinitrophenylhydrazine, melting at 122°. Allylacetylacetone (VI).-Similarly, 140 g. (1 mole) of VI was treated with 3.5 moles of sodium acetylide. Fractionation of the products gave 14 g., 20% yield, of allylacetone, b.p. 69°at 100 mm., w25d 1.4178; 2,4-dinitrophenylhydrazone, m.p. 103-104°( lit. 104°14); 39 g., 36%,, of unreacted VI, b.p. 82-84°at 16 mm., derivative with 2,4-dinitrophenylhydrazine, m.p. 185-186°, and a residue of 56 g., 56%yield, of crude allylacetylacetone amine (VIII), m.p. 63-66°, recrystallized from low boiling Skellysolve, m.p. 65-67°; derivative with 2,4-dinitrophenylhydrazine, m.p. 185-186°.On heating VIII with 10% sodium hydroxide, ammonia was (13) R. L. Shriner and R. C. Fuson, "Identification of Organic Compounds," 3rd ed.,