Abstract
Study of the reactions of compounds of the norbornene series demonstrated that the AgNO2-SOCl2 and AgNO3-SOCl2 systems serve as nitrosochlorinating agents under the conditions of electrophilic addition. X-ray diffraction study showed that dimerization of cis-exo-2-chloro-3-nitrosobicyclo[2.2.1]heptane occurs heterostereospecifically. The origin of the active principle of the reagents is discussed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
O. B. Bondarenko, A. Yu. Gavrilova, V. N. Tikhanushkina, and N. V. Zyk, Izv. Akad. Nauk, Ser. Khim., 2005, 2070 [Russ. Chem. Bull., Int. Ed., 2005, 54, 0000].
N. S. Zefirov, N. V. Zyk, Yu. A. Lapin, E. E. Nesterov, and B. I. Ugrak, J. Org. Chem., 1995, 60, 6771.
N. V. Zyk, Yu. A. Lapin, E. E. Nesterov, B. I. Ugrak, and N. S. Zefirov, Zh. Org. Khim., 1995, 31, 840 [Russ. J. Org. Chem., 1995, 31 (Engl. Transl.)].
Yu. A. Lapin, Ph. D. (Chem.) Thesis, Department of Chemistry of the M. V. Lomonosov Moscow State University, Moscow, 1989, 157 pp. (in Russian).
G. H. Hakimelahi, H. Sharghi, H. Zarrinmayeh, and A. Khalafi-Nezhad, Helv. Chim. Acta, 1984, 67, 906.
M. M. Rogic, T. R. Demmir, R. Fuhrmann, and F. W. Koft, J. Am. Chem. Soc., 1975, 97, 3241.
R. Glaser, R. K. Murmann, and C. L. Barnes, J. Org. Chem., 1996, 61, 1047.
N. S. Zefirov and I. V. Bodrikov, Zh. Org. Khim., 1983, 19, 2225 [J. Org. Chem. USSR, 1983, 19 (Engl. Transl.)].
J. D. Roberts, E. R. Trumbull, W. Bennett, and R. Armstrong, J. Am. Chem. Soc., 1950, 72, 3116.
C. D. Ver Nooy and C. S. Rondestvedt, J. Am. Chem. Soc., 1955, 77, 3583.
J. Meinwald, Y. C. Meinwald, and T. N. Baker, J. Am. Chem. Soc., 1964, 86, 4074.
J. B. Miller, J. Org. Chem., 1961, 26, 4905.
B. W. Ponder and P. W. Wheat, J. Org. Chem., 1972, 37, 543.
L. Schriver-Mazzuoli, A. Hallou, and A. Schriver, J. Phys. Chem. A, 1998, 102, 9772.
R. A. Ogg and M. K. Wilson, J. Chem. Phys., 1950, 18, 900.
R. Ryason and M. K. Wilson, J. Chem. Phys., 1954, 22, 2000.
The Chemistry of Nitro and Nitroso Groups, Part 1, Ed. Y. Feuer, Interscience, New York, 1969.
D. Cook, S. J. Kuhn, and G. A. Olah, J. Chem. Phys., 1960, 33, 1669.
N. V. Zyk, A. V. Nikulin, S. I. Kolbasenko, A. G. Kutateladze, and N. S. Zefirov, Zh. Org. Khim., 1984, 20, 1329 [J. Org. Chem. USSR, 1984, 20 (Engl. Transl.)].
A. J. Gordon and R. A. Ford, The Chemist’s Companion, A Wiley-Interscience Publication, J. Wiley and Sons, New York-London-Sydney-Toronto, 1972.
L. J. Beckman, W. A. Fessler, and M. A. Kise, Chem. Rev., 1951, 48, 319.
G. M. Sheldrick, SHELXL97. Program for Crystal Structure Refinement, Göttingen Universität, Göttingen (Germany), 1997.
Author information
Authors and Affiliations
Additional information
Dedicated to Academician N. S. Zefirov on the occasion of his 70th birthday.
For Part 1, see Ref. 1.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2081–2085, September, 2005.
Rights and permissions
About this article
Cite this article
Bondarenko, O.B., Gavrilova, A.Y., Tikhanushkina, V.N. et al. New systems for classical nitrosohalogenation of alkenes 2. Generation of nitrosyl chloride in AgNO2-SOCl2 and AgNO3-SOCl2 systems. Russ Chem Bull 54, 2145–2149 (2005). https://doi.org/10.1007/s11172-006-0089-2
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0089-2