Abstract
The 1-hydroxy-2-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-phenylethyl cation generated under “long life” conditions undergoes fragmentation to afford 5H-dibenzo[a,d]cycloheptenyl-and methylphenylhydroxycarbinyl canons but does not undergo carbocationic cyclization.
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References
J. P. Kennedy,Cationic Polymerization of Olefins: A Critical Inventory, Wiley, New York, 1975, 337; H. Mayr,Angew. Chem., Int. Ed. Engl., 1990,29, 1371.
C. X. Grob and P. W. Schiess,Angew. Chem., 1967,79, 1; C. A. Grob, Angew. Chem., 1969,81, 543; D. M. Brouwer and J. A. Van Doom,Rec. Trav. Chim., 1971,90, 535.
R. Conrow,J. Am. Chem. Soc., 1959,81, 5461.
M. D. Stanescu and S. A. Osadchii,Bul. Inst. Politeh. Bucuresti, Ser. Chim.-Metal., 1991,53, 107.
G. Berti,J. Org. Chem., 1957,22, 230.
K. Yates and B. F. Scott,Can. J, Chem., 1963,41, 2323.
E. Cioranescu, M. Banciu, R. Jelescu, M. Rentzea, M. Elian, and C. D. Nenitzescu,Tetrahedron Lett., 1969, 1871; W Voicu and F. Badea,Rev. Roum. Chim., 1969,14, 911, 929; M. Stanescu, G. Minai, L. Stanescu, and E. Cioranescu,Rev. Roum. Chim., 1979,24, 197; M. Stanescu, M. Elffan, and E, Cioranescu,Rev. Roum. Chim., 1987,32, 969.
M. Elifan,Rev. Roum. Chim., 1990,35, 281; M. Nogradi, W. D. Ollis, and I. O. Sutherland,Chem. Commun., 1970, 158.
G. Olah and G. Liand,J. Org. Chem., 1975,40, 2108; T. Birchall and R. G. Gillespie,Can. J. Chem., 1966,43, 1045
M. Bohshar, H. Heydt, and M. Regitz,Tetrahedron, 1986,42, 1815.
A. C. Razus, E. Bartha, Zs. Arvay, S. A. Osadchii, V. I. Mamatyuk, and V. G. Shubin,Rev. Roum. Chim., 1991,36, 1307.
S. A. Osadchii, M. P. Polovinka, D. V. Korchagina, N. A. Pankrushina, Zh. V. Dubovenko, V. A. Barkhash, and V. A. Koptyug,Zh. Org. Khim., 1981,17, 1211 [J. Org. Chem. USSR, 1981,17 (Engl. Transl.)].
B. Bodo, J. Andrieux, and D. Molho,C. R. Acad. Sci., Ser. C, 1971,273, 170.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 397–399, February, 1996.
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Osadchii, S.A., Stanescu, M.D., Mamatyuk, V.I. et al. Fragmentation of 1-hydroxy-2-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-phenylethyl cation in superacid. Russ Chem Bull 45, 381–383 (1996). https://doi.org/10.1007/BF01433977
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DOI: https://doi.org/10.1007/BF01433977