I. Bis-diazo Alkanes II. Polymeric Acyl-Ureides and N-Carbethoxy Ureas III. The Action of Hydrazine on Polychloro Compounds

Abstract

The problem of this dissertation consisted in the preparation of N,N'-dinitroso compounds, as intermediates for the prepa ration of the corresponding bis-diazo alkanes. These were then allowed to react with carboxylic acids, phenols, aldehydes, and ketones. The bis-diazo alkanes were also used as crosslinking agents for certain linear polymers, such as ethyl cellulose, polyacrylic and polymethacrylic acids. The bis-diazo alkanes have been prepared from the corresponding N-nitroso compounds by the decomposition of the latter by alkali. The follovling N, N' -dinitroso compounds have been prepared: 1. N,N'-Dinitroso-1,2-diureidoethane (m.p. 182.9-183.9°C.) 2. N,N'-Dinitroso-1,6-Diureidohexane (m.p. 138-139°C.) 3. N,N'-Dinitroso-N,N'-dicarbomethoxy-1,2-diaminobutane (m.p. 101.6°C.) 4. N,N'-Dinitroso-N,N'-dicarbomethoxy-1,4-diaminobutane (m.p. 87.4°C.) 5· N,N'-Dinitroso-N, N'-dicarbomethoxy-1,6-diaminohexane (m.p. 61.2- 62.6°C.) 6. N,N'-Dinitroso-N,N'-dicarbethoxy-1,2-di aminoethane(Liquid) 7. N,N'-Dinitroso-N,N'-dicarbethoxy-1,4-diaminobutane(Liquid) 8. N , N' - Di r:.i troso-N , N' -dicarbethoxy-1,6-diaminohexane (Liquid) 9. 4,4,13,13-Tetramethyl-N,N'-dinitroso-5,12-diaza-2,15-hexa- decanedione(83.5-84 c.) 10. 4,4,11,11 -Tetramethyl -N , N '-di ni troso-5,10-diaza-2,15-~etradecanedione (146·. 7-147. 7°C.) 11. 4,4, 9, 9-Tetramethyl-N ,N' -dinitroso-5,8 -diaza-2,ll-dodecanedione (l53·2-154.00C.) The first five and the last t wo compounds are slightly soluble in absolute ethyl alcohol and ethyl ether. The solubility of the last three compounds in alcohol decreases as we go from (9) to (10 ). Compounds (6)(7) and (8) are viscous liquids, and are very soluble in cold alcohol, ether and in chloroform. In the presence of aqueous acids or moisture, the above compounds decompose slowly back into the unnitroaated compounds. They decompose slowly on heating and completely at about their melting points.[truncated]