References
- Michejda , C. J. , Kroeger-Koepke , M. B. , Koepke , S. R. and Sieh , D. E. 1981 . “N-Nitroso Compounds” , ACS Symposium Series, No. 174 Edited by: Scanlan , R. A. and Tannebaum , S. R. Washington, D. C. : American Chemical Society . Ch. 1
- Mochizuki , M. , Anjo , T. and Okada , M. 1980 . Tetrahedron Lett. , 21 : 3693
- Bailey , P. S. 1982 . “Ozonation in Organic Chemistry,” , Vol. II , New York : Academic Press . Ch. 9
- Challis , B. C. and Challis , J. A. 1982 . “Supplement F. The Chemistry of Amino, Nitroso, and Nitro Compounds and Their Derivatives” , Edited by: Patai , S. New York, NY : John Wiley and Sons . Part 2, Ch. 26
- Lyle , R. E. , Saavedra , J. E. and Lyle , G. G. 1976 . Synthesis , 462
- Emmons , W. D. and Freeman , J. P. 1955 . J. Am. Chem. Soc. , 77 : 4387 Dibenzhydrylnitramine (lc) was prepared for comparison from the reaction of acetone cyanohydrin nitrate (Wateree Chem. Co., Camden, South Carolina) and dibenzhydrylamine. Attempted purification of a small amount of the crude product (a white foam showing no starting amine by NMR) by passage through a small column of silica gel gave only the starting amine in nearly quantitative yield. Recrystallization from ethyl acetate-chloroform gave 2.49 g (63%) of white crystals. By raising the temperature rapidly (20°/min), the unusually broad melting range could be narrowed to 193–200°. The clear melt soon solidified at this temperature and remelted to a yellow liquid at 255–290° similar to that obtained by slowly heating the substance (2°/min) to these temperatures. NMR (CDC13): δ 5.20 (s, 2H) and 7.1–7.8 (m, 20 H); MS (70 eV): m/e 349 (M-45), 272 (M-122), 242 (M-152), 212 (M-182), and 167 (M-227)
- Hauser , C. R. , Brasen , W. R. , Skell , P. S. , Kantor , S. W. and Brodhag , A. E. 1956 . J. Am. Chem. Soc. , 78 : 1653
- Karabatsos , G. J. and Taller , R. A. 1964 . J. Am. Chem. Soc. , 86 : 4373