Conclusions
-
1.
Polarography has been used to study the kinetics of the pseudomonomolecular reactions of α-allene bromides with amines.
-
2.
Reactions of α-bromoallene derivatives containing either a hydrogen atom, or an alkyl substitutent at the bromoallene carbon atom, with neutral nucleophiles such as piperidine are overall second-order processes which follow a bimolecular SN2′ type nucleophilic substitution mechanism.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
M. V. Mavrov, E. S. Voskanyan, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 884 (1960).
M. V. Mavrov, E. S. Voskanyan (Voskanjan), and V. F. Kucherov, Tetrahedron,25, 3277 (1969).
M. V. Mavrov, A. P. Rodionov, and V. F. Kucherov, Tetrahedron Lett., 759 (1973).
W. Kirmse, Carbene Chemistry, Academic Press, New York (1971), p. 14.
P. J. Stang, Progress Phys. Org. Chem.,10, 205 (1973).
Z. Rappoport, Advan. Phys. Org. Chem.,7, 1 (1969).
G. Modena and U. Tonellato, Advan. Phys. Org. Chem.,9, 185 (1971).
J. Miller, Aromatic Nucleophilic Substitution, Elsevier, Amsterdam (1968), Chap. 6.
J. J. Christensen, R. M. Izatt, D. P. Wrathall, and L. D. Hansen, J. Chem. So., A, 1212 (1969).
A. D. George, E. Doomes, and N. H. Cromwell, J. Org. Chem.,36, 3918 (1971).
K. Laidler, Kinetics of Organic Reactions [Russian translation], Mir (1966).
A. N. Zaidel', Errors in the Measurement of Physical Quantities [in Russian], Leningrad, Nauka (1974).
M. V. Mavrov, A. P. Rodionov, E. P. Prokof'ev, and V. F. Kucherov, Zh. Org. Khim.,9, 658 (1973).
K. Ingold, Theoretical Principle of Organic Chemistry [Russian translation], Mir (1973), Chap. 7.
F. G. Bordwell, Accounts Chem. Res.,3, 281 (1971).
M. V. Mavrov, E. S. Voskanyan, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 2774 (1967).
M. V. Mavrov, A. P. Rodionov, V. M. Shitkin, S. D. Kulomzina, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 948 (1973).
S. R. Landor, A. N. Patel, P. F. Whiter, and P. M. Greaves, J. Chem. Soc., C, 1223 (1966).
J. Simonet, M. Doupeux, P. Martinet, and D. Bretelle, Bull. Soc. Chim. France, 3930 (1970).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 564–567, March, 1977.
The authors wish to thank S. S. Yufit for his interest in this work, and for a discussion of the results obtained in it.
Rights and permissions
About this article
Cite this article
Mavrov, M.V., Rodionov, A.P., Gul'tyai, V.P. et al. Kinetics of the reactions of α-allene bromides with amines. Russ Chem Bull 26, 506–509 (1977). https://doi.org/10.1007/BF01179454
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01179454