Abstract
Macrocycle opening in derivatives of benzocrown ethers under the action of amines is affected by the nature of the heteroatoms in the macrocycle, the nature of the functional group in the benzene ring of the crown ether, and the length, branching, and number of hydrocarbon radicals at the amine nitrogen atom. A distinguishing feature of this reaction is the template effect of MeNH3 +, Me2NH2 +, Na+, and K+ ions.
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S. P. Gromov, A. 1. Vedernikov, and O. A. Fedorova,Izv. Akad. Nauk, Ser. Khim., 1995, 950 [Russ. Chem. Bull., 1995,44, (Engl. Transl.)].
R. Hoss and F. Vogue,Angew. Chem. Int. Ed. Engl., 1994,33, 375.
S. P. Gromov, O. A. Fedorova, A. I. Vedernikov, V. V. Samoshin, N. S. Zefirov, and M. V. Alfimov,Izv. Akad. Nauk, Ser. Khim., 1995, 121 [Russ. Chem. Bull., 1995,44, 116 (Engl. Transl.)].
R. M. Izatt, K. Pawlak, J. S. Bradshaw, and R. L. Bruening,Chem. Rev., 1991,91, 1721.
S. P. Gromov, M. V. Fomina, and M. V. Alfimov,Izv. Akad. Nauk, Ser. Khim., 1993, 1625 [Russ. Chem. Bull., 1993,42, 1561 (Engl. Transl.)].
S. S. Lee, S. O. Park, J. H. Jung, B. Y. Lee, and S. J. Kim,Bull. Korean Chem. Soc., 1990,11, 276.
J. M. Lehn and P. Vierling,Tetrahedron Lett., 1980,21, 1323.
F. de Jong, D. N. Reinhoudt, and R. Huis,Tetrahedron Lett., 1977, 3985.
R. M. Izatt, N. E. Izatt, B. E. Rossiter, J. J. Christensen, and B. L. Haymore,Science, 1978,199, 994.
L. G. Yudin, A. V. Blokhin, Yu. G. Bundel, B. Ya. Simkin, and V. I. Terenin,Zh. Org. Khim., 1983,19, 2361 [J. Org. Chem. USSR, 1983,19 (Engl. Transl.)].
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 687–692, March, 1996.
For Part I see Ref. 1.
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Gromov, S.P., Vedernikov, A.I. & Fedorova, O.A. Macrocycle opening in crown ethers. Russ Chem Bull 45, 648–653 (1996). https://doi.org/10.1007/BF01435799
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DOI: https://doi.org/10.1007/BF01435799