Organic Chemistry of Explosives

(coco) #1

62 Synthetic Routes to AliphaticC-Nitro


39 , 401; (c) P. E. Eaton, N. Gelber, R. Gilardi, S. Iyer, R. Surapaneni and M. -X. Zhang,Propell.
Explos. Pyrotech., 2002, 27 ,1.


  1. R. D. Gilardi and J. Karle, inChemistry of Energetic Materials, Eds. D. R. Squire and G. A. Olah,


Academic Press, San Diego, CA, 2 (1991).


  1. R. R. Fraser, T. S. Mansour and S. Savard,J. Org. Chem., 1985, 50 , 3232.

  2. L. W. Kissinger and H. E. Ungnade,J. Org. Chem., 1958, 23 , 1340.

  3. V. M. Belikov, L. V. Ershova, V. N. Goditidze and S. S. Novikov,Izv. Akad. Nauk USSR, Otd. Khim.


Nauk., 1959, 943;Chem. Abstr., 1960, 54 , 259g.


  1. L. Zalvkaev and E. Vanag,J. Gen. Chem. USSR, 1956, 26 , 657.

  2. J. Bredt,Chem. Ber., 1881, 14 , 1780; 1882, 15 , 2318.

  3. V. Grakauskas and A. M. Guest,J. Org. Chem., 1978, 43 , 3485.

  4. R. B. Kaplan and H. Shechter,J. Am. Chem. Soc., 1953, 75 , 3980.

  5. M. J. Kamlet,NAVORD Rep. 6206, US Naval Ordnance Lab, Whiteoak, Maryland (1959).

  6. H. G. Adolph and M. J. Kamlet,Proc.7thInternational Symposium on Detonation,USNaval


Academy, Annapolis, Maryland, Vol. 1, 60 (1981).


  1. K. Klager and R. R. Rindone, ‘Development of an efficient Process to Manufacture Bis(2-fluoro-2,2-


dinitroethyl)formal (FEFO)’, 18thInternational Annual Conference of ICT, Karlsruhe, Germany,
28/1–28/14 (1987).


  1. V. Grakauskas and K. Baum,J. Org. Chem., 1968, 33 , 3080.

  2. (a) A. L. Fridman, F. A. Gabitov, E. A. Ponomareva, Yu. N. Senichev,Zh. Obshch. Khim., 1968,


38 , 1902; Engl. Tranl., 1850; (b) M. J. Kamlet and H. G. Adolph,J. Org. Chem., 1968, 33 , 3073;
(c) H. G. Adolph,US Pat. 3 446 857 (1969).


  1. M. A. Besprozvannyi, A. A. Fainzilberg, G. Kh. Khismamutdinov, M. Sh. Lvova, V. O. Slovetskii


and O. G. Usyshkin,Izv. Akad. Nauk USSR, Ser. Khim. (Engl. Transl.), 1971, 20 , 2397.


  1. R. J. Spear and W. S. Wilson, ‘Recent Approaches to the Synthesis of High Explosive and Energetic
    Materials’,J. Energ. Mater., 1984, 2 , 61–149.

  2. I. J. Dagley and R. J. Spear, ‘Synthesis of Organic Energetic Compounds’, inOrganic Energetic


Compounds, Ed. P. L. Marinkas., Nova Science Publishers Inc., New York, Chapter 2, 47–163
(1996).


  1. H. L. Cates Jr and H. Shechter,J. Org. Chem., 1961, 26 , 51.

  2. A. L. Krieger, C. S. Rondestvedt and M. Stiles,Tetrahedron, 1963, 19 , Suppl. 1, 197.

  3. P. O. Tawney,US Pat. 3 050 565 (1962);Chem. Abstr., 1963, 58 , 1350a.

  4. R. E. Cochoy, R. R. McGuire and S. A. Shackelford,J. Org. Chem., 1992, 57 , 2950.

  5. K. Baum and V. Grakauskas, ‘Research in Fluoro-Nitro Compounds’,Report 2099, Nov 7, 1961,


Contract Nonr-2655(00), Available from Defence Technical Information Center, Cameron Station,
Alexandria, VA 22304-6145.


  1. R. E. Cochoy, R. R. McGuire and S. A. Shackelford,J. Org. Chem., 1990, 55 , 1401.

  2. H. Feuer and R. Harmetz,J. Org. Chem., 1961, 26 , 1061.

  3. H. Feuer, G. Leston, R. Miller and A. T. Nielsen,J. Org. Chem., 1963, 28 , 339.

  4. R. D. Geckler, M. H. Gold and L. Herzog,J. Am. Chem. Soc., 1951, 73 , 749.

  5. H. Feuer and U. E. Lynch-Hart,J. Org. Chem., 1961, 26 , 391.

  6. J. C. Dacons, J. C. Hoffsommer and M. J. Kamlet,J. Org. Chem., 1961, 26 , 4881.

  7. I. S. Korsakova, S. S. Novikov and M. A. Yatskovskaya,Dokl. Akad. Nauk USSR, 1958, 118 , 954.

  8. N. N. Bulatova, I. S. Korsakova and S. S. Novikov,Zh. Obshch. Khim., 1959, 29 , 3659.

  9. W. H. Gilligan and M. Graff,J. Org. Chem., 1968, 33 , 1247.

  10. H. Feuer, S. M. Pier and E. H. White,J. Org. Chem., 1961, 26 , 1639.

  11. M. B. Frankel,Tetrahedron, 1963, 19 , Suppl. 1, 213.

  12. E. Hamel, J. P. Kispersky and K. Klager,J. Org. Chem., 1961, 26 , 4368.

  13. H. Shechter and L. Zeldin,J. Am. Chem. Soc., 1951, 73 , 1276.

  14. K. Baum and V. Grakauskas,J. Org. Chem., 1969, 34 , 3927.

  15. K. Baum and A. M. Guest,Synthesis, 1979, 311.

  16. H. G. Adolph,US Pat. 453 675 (1983);Chem. Abstr., 1983, 99 , 194427g.

Free download pdf