Abstract
The electrochemical behavior of a series of halogen-containing cyclohexa-2,5-dien-1-ones at the glassy-carbon electrode in DMF was studied. The reductive dehalogenation of 2-bromo-5-dibromomethyl-4-dichloromethyl-4-methylcyclohexa-2,5-dien-1-one first results in the elimination of the carbonylallylic bromine atoms, then the carbonylic bromine atom is elimi-nated, and finally, the neopentylic chlorine atoms are eliminated.
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References
C. K. Mann and K. K. Barnes, Electrochemical Reactions in Nonaqueous Systems, Marcel Dekker, New York, 1970.
Organic Electrochemistry, Eds M. M. Baizer and H. Lund, Marcel Dekker, New York-Basel, 1983.
K. P. Butin, Usp. Khim., 1971, 40, 1058 [Russ. Chem. Rev., 1971, 40 (Engl. Transl.)].
E. Blair, J. Greaves, and P. J. Farmer, J. Am. Chem. Soc., 2004, 126, 8632.
K. Janagita, I. Sagami, and T. Shimizu, Chem. Lett., 1997, 561.
R. Shanker and W. A. Atkins, Biotechnol. Prog., 1996, 474.
R. Janagita, I. Sagami, S. Daff, and T. Shimizu, Biochem. Biophys. Res. Commun., 1988, 249, 678.
H. Chen, J. Shockcor, W. Chen, R. Espina, L.-S. Gan, and A. E. Mutlib, Chem. Research in Toxicology, 2002, 15, 388.
Entsiklopediya lekarstv [Encyclopedia of Medicines], Registr Lekarstvennykh Sredstv, Moscow, 2005 (in Russian).
E. Ravina, I. M. Montanes, M. T. Cobreros, and F. Tato, Chim. Ther., 1973, 8, 290.
L. Minale, G. Gimino, S. De Stefano, and G. Sodano, Fortshr. Chem. Org. Naturst., 1976, 33, 1.
J. E. Thompson, R. P. Walker, and D. J. Faulkner, Mar. Biol., 1985, 83, 11.
N. B. Perry, J. W. Blunt, and M. H. G. Munro, Tetrahedron, 1988, 44, 1727.
M. H. G. Munro, J. W. Blunt, G. Barns, C. N. Battershill, R. J. Lake, and N. B. Perry, Pure Appl. Chem., 1989, 61, 529.
K. P. Butin, A. A. Ivkina, and V. N. Shishkin, Zh. Org. Khim., 1985, 21, 150 [J. Org. Chem. USSR, 1985, 21 (Engl. Transl.)].
K. P. Butin, A. A. Ivkina, V. N. Shishkin, and B. S. Tanaseichuk, Izv. Akad. Nauk SSSR, Ser. Khim., 1983, 98 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1983, 32 (Engl. Transl.)].
K. P. Butin, A. A. Moiseeva, V. I. Rozenberg, T. V. Magdesieva, and E. V. Sergeeva, Izv. Akad. Nauk, Ser. Khim., 1994, 839 [Russ. Chem. Bull., 1994, 43, 783 (Engl. Transl.)].
G. V. Gavrilova, V. A. Nikanorov, V. I. Bakhmutov, A. A. Gavrilov, V. I. Rozenberg, and O. A. Reutov, Metalloorg. Khim., 1990, 3, 299 [Organomet. Chem. USSR, 1990, 3 (Engl. Transl.)].
G. V. Gavrilova, V. A. Nikanorov, N. V. Polyakova, A. A. Gavrilov, P. B. Terent’ev, V. I. Rozenberg, and O. A. Reutov, Metalloorg. Khim., 1989, 2, 929 [Organomet. Chem. USSR, 1989, 2 (Engl. Transl.)].
O. A. Reutov, A. L. Kurts, and K. P. Butin, Organicheskaya khimiya [Organic Chemistry], Binom, Moscow, 2004, Vol. 2, p. 101 (in Russian).
G. V. Gavrilova, A. A. Gavrilov, D. P. Krut’ko, and K. P. Butin, Zh. Org. Khim., 2003, 31, 393 [Russ. J. Org. Chem., 2003, 31 (Engl. Transl.)].
E. J. Friedrich, J. Org. Chem., 1968, 33, 413.
K. Anwers and R. Ziegler, Justus Liebigs Ann. Chem., 1921, 425, 295.
F. J. Bordwell and K. M. Wellman, J. Org. Chem., 1963, 28, 2544.
H. E. Zimmerman, P. Hackett, D. F. Juers, J. M. McCall, and B. Schröder, J. Am. Chem. Soc., 1971, 93, 3653.
K. L. Cook and A. J. Waring, J. Chem. Soc., Perkin Trans. 1, 1973, 529.
V. A. Nikanorov, G. V. Gavrilova, V. I. Rozenberg, and O. A. Reutov, Izv. Akad. Nauk SSSR, Ser. Khim., 1984, 2647 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1984, 33, 2428 (Engl. Transl.)].
V. A. Nikanorov, G. V. Gavrilova, V. I. Rozenberg, and O. A. Reutov, Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 2345 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987, 36, 2174 (Engl. Transl.)].
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1558–1564, September, 2006.
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Gavrilova, G.V., Moiseeva, A.A., Beloglazkina, E.K. et al. Electrochemical study of the sequence of reductive dehalogenation of 2-bromo-5-dibromomethyl-4-dichloromethyl-4-methylcyclohexa-2,5-dien-1-one and its analogs. Russ Chem Bull 55, 1617–1623 (2006). https://doi.org/10.1007/s11172-006-0463-0
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DOI: https://doi.org/10.1007/s11172-006-0463-0