Abstract
An electrochemical method for the synthesis of geminal azidonitro compounds was developed. The method involves electrooxidative coupling of azide anions with salts of nitro compounds and affords geminal azidonitroalkanes, azidonitrocycloalkanes, and diazidodinitrocycloalkanes in 45–92% yields.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
G. K. S. Prakash, J. J. Struckhoff, Jr., K. Weber, A. Schreiber, R. Bau, and G. A. Olah, J. Org. Chem., 1997, 62, 1872.
I. V. Tselinskii, S. F. Mel’nikova, and S. A. Fedotov, Izv. Akad. Nauk, Ser. Khim., 2002, 1354 [Russ. Chem. Bull., Int. Ed., 2002, 51, 1466]
S. I. Al-Khalil and W. R. Bowman, Tetrahedron Lett., 1982, 43, 4513.
S. I. Al-Khalil and W. R. Bowman, J. Chem. Soc., Perkin Trans. 1, 1986, 555.
B. G. Christensen and L. D. Cama, Ger. Offen., 2 151 036; Chem. Abstr., 1972, 77:126616.
S. M. Wright and G. A. Ward, J. Electrochem. Soc., 1965, 2, 11.
N. L. Weinberg and H. R. Weinberg, Chem. Rev., 1968, 68, 489.
R. Haul and E. Scholz, Naturwissenschaften, 1944, 32, 294.
S. Wawszonek and T.-Y. Su, J. Electrochem. Soc., 1973, 120, 745.
B. C. Gilbert and R. O. C. Norman, Can. J. Chem., 1982, 60, 1379.
V. A. Kokorekina, V. A. Petrosyan, and L. G. Feoktistov, Elektrosintez monomerov [Electrochemical Synthesis of Monomers], Nauka, Moscow, 1980, 83 (in Russian); S. T. Bahner, Ind. Eng. Chem., 1952, 44, 317.
N. Kornblum, H. O. Larson, R. K. Blackwood, D. D. Mooberry, E. P. Oliveto, and G. E. Graham, J. Am. Chem. Soc., 1956, 78, 1497.
G. A. Olah, P. Ramaiah, G. K. S. Prakash, and R. Gilardi, J. Org. Chem., 1993, 58, 763.
A. T. Nielson, J. Org. Chem., 1962, 27, 1993.
K. Fukunaga and M. Kimura, J. Chem. Soc. Jpn, Chem. Ind. Chem., 1982, 1499.
D. W. Chasar, Synthesis, 1982, 841.
G. Rosini, E. Marotta, R. Ballini, and M. Petrini, Synthesis, 1986, 237.
Author information
Authors and Affiliations
Additional information
__________
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2452–2457, November, 2004.
Rights and permissions
About this article
Cite this article
Ogibin, Y.N., Ilovaisky, A.I., Merkulova, V.M. et al. Electrochemical synthesis of geminal azidonitro compounds. Russ Chem Bull 53, 2558–2563 (2004). https://doi.org/10.1007/s11172-005-0154-2
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-005-0154-2