Formation of Urea, Isourea, and Triazine Derivatives from Diisopropylcyanamide with Trifluoroacetic Anhydride and Trifluoromethanesulfonic Anhydride: Thermal Instability of Urea and Isourea Derivatives

Journal of Organic Chemistry

Volumn 62, Issue 26, 1997, Pages 9070-9075

  Norris, William P ^a   Merwin, Lawrence H ^a   Ostrom, Gregory S ^a   Gilardi, Richard D ^b  

^a NAVAL AIR WARFARE CENTER   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542632813     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9710184     Document Type: Article

References (21)

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14. Barton, D. H. R.; Elliott, J. D.; Gero, S. D. J. Chem. Soc., Perkin Trans. 1 1982, 2085-2090.
15. 19F NMR integral and t = 0-9000 s.
16. van der Zand, M. K. H. M. Recl. Trav. Chim. Pays-Bas 1889, 8, 221-247.
17. Boiko, V. I.; Samari, L. I. Ukr. Khim. Zh. 1992, 58, 797-798.
18. 2w = 0.1557 for 2126 unique observed [I > 2σ(I)] reflections. The authors have deposited X-ray crystallographic data for the structure of compound 15 with the Cambridge Crystallographic Data Center. The data can be obtained, upon request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
19. 19F NMR data, obtained from the thermolysis reaction mixtures, are compatible with the structures.
20. Lindner, E.; von Au, G.; Eberle, H.-J. Chem. Ber. 1981, 114, 810-813. This refers to the cleavage of the cyclic ether tetrahydro-2H-pyran by triflic anhydride. However, in the present work diethyl ether solvent is not cleaved by triflic anhydride.
21. The isopropyl methine proton signal, at 27°C, was so broad as to be undetectable. At the higher temperature used, an unresolved broad band developed, indicating its position in the spectrum.