Abstract
1-Phosphoryl-substituted cyclopropanes, cyclobutanes, and cyclopentanes were obtained by the reaction of phosphoryl-substituted esters and nitriles of acetic acid with α,ω-dihaloalkanes. The influence of the CH-acidity of the starting compounds and electrophilicity of the alkylating agent on the reaction rate was examined.
Similar content being viewed by others
Literature cited
T. Hirao, M. Hagihara, and T. Agawa, Bull. Chem. Soc. Jpn.,58, No. 11, 3104 (1985).
D. Seyferth and R. S. Harmor, J. Org. Chem.,36, No. 1, 128 (1971).
D. Seyferth, R. S. Harmor, and P. Hilbert, J. Org. Chem.,36, No. 10, 1379 (1971).
R. D. Gordeev and A. M. Pudovik, Zh. Obshch. Khim.,49, No. 4, 728 (1979).
L. Maier, Phosphorus Sulfur,14, No. 3, 295 (1983).
H. Schmidbaur and T. Pollok, Helv. Chim. Acta,67, No. 8, 2175 (1984).
W. H. Perkin, Ber.,1, 1739 (1983).
N. S. Zefirov, T. S. Kuznetsova, S. I. Kozhushkov, et al., Zh. Org. Khim.,19, No. 2, 541 (1983).
M. M. Gantaeva, Candidate of Chemical Sciences Dissertation, Baku (1987).
P. V. Kazakov, L. V. Kovalenko, I. L. Odinets, and T. A. Mastryukova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2150 (1989).
É. S. Petrov, E. N. Tsvetkov, M. I. Terekhova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 534 (1976).
É. S. Petrov, E. N. Tsvetkov, S. P. Mesyats, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 782 (1976).
M. I. Kabachnik and T. A. Mastryukova, Dokl. Akad. Nauk SSSR,260, No. 4, 893 (1981).
A. G. Matveeva, M. I. Terekhova, N. P. Nesterova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2067 (1988).
M. Fedozynskii, K. Wojciechowski, Z. Matacz, and M. Makosza, J. Org. Chem.,43, No. 24, 4682 (1978).
A. Gordon and R. Ford, A Chemist's Companion: A Handbook of Practical Data, Techniques, and Reference, Wiley-Interscience, New York (1973).
D. J. Martin and C. E. Ciziffin, J. Org. Chem.,30, No. 12, 4034 (1965).
A. N. Pudovik and N. M. Lebedeva, Zh. Obshch. Khim.,25, No. 12, 2235 (1955).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1873–1880, August, 1990.
Rights and permissions
About this article
Cite this article
Kazakov, P.V., Odinets, I.L., Laretina, A.P. et al. Cycloalkylation of compounds in the series of phosphorus-substituted derivatives of acetic acid. Russ Chem Bull 39, 1702–1708 (1990). https://doi.org/10.1007/BF00961505
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00961505