Generation of free radicals by reaction of some organotin and orga n omer cur y compounds with bromine
Organic and Biological Chemistry
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Conclusions
- 1.
The dark bromodemetalation of a number of organotin and organomercury compounds in toluene or p-fluorotoluene initiates the free-radical bromination of the solvents in the methyl group, which testifies to the generation of free radicals during bromodemetalation.
- 2.
A halodemetalation mechanism was proposed, which postulates that donor-acceptor complexes between the reactants, in which the organometallic compound functions as the donor and the halogen functions as the acceptor, take part in the reaction. The mechanism makes it possible to interpret the results obtained in the study (generation of radicals), as well as the previously observed generation of carbcations in the given reaction.
Keywords
Methyl Toluene Free Radical Bromine Halogen
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Literature cited
- 1.F. R. Jensen and B. Rickborn, Electrophilic Substitution on Organomercurials, McGraw-Hill, New York (1968).Google Scholar
- 2.O. A. Reutov, I. P. Beletskaya, and V. I. Sokolov, Reaction Mechanisms of Organometallic Compounds [in Russian], Khimiya (1972).Google Scholar
- 3.I. P. Beletskaya, O. A. Reutov, and T. A. Azizyan, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 223 (1962).Google Scholar
- 4.O. A.Reutov, É. V. Uglova, I. P. Beletskaya, and T. B. Svetlanova, Izv. Akad. Nauk SSSR, Ser. Khim., 1383 (1964).Google Scholar
- 5.S. Boué, M. Gielen, and J. Nasielskii, J. Organometal. Chem.,9, 461 (1961).Google Scholar
- 6.See [1], p. 80.Google Scholar
- 7.G. A. Razuvaev, K. S. Minsker, and Yu. A. Sangalov, Dokl. Akad. Nauk SSSR,159, 158 (1964).Google Scholar
- 8.C. F. Lane and H. C. Brown, J. Amer. Chem. Soc.,92, 7212 (1970).Google Scholar
- 9.É. V. Uglova and T. B. Svetlanova, Data of First All-Union Conference on Dynamical Stereochemistry and Conformational Analysis [in Russian], Izd. Odessk. Univ., Odessa (1970), p. 98.Google Scholar
- 10.G. A. Razuvaev, K. S. Minsker, and Yu. A. Sangalov, Dokl. Akad. Nauk SSSR,158, 170 (1964).Google Scholar
- 11.K. A. Bilevich and O. Yu. Okhlobystin, Usp. Khim.,37, 2568 (1968).Google Scholar
- 12.G. B. Sergeev and I. A. Leenson, Usp. Khim.,41, 1566 (1972).Google Scholar
- 13.Z. V. Todres, Zh. Vses. Khim. Obshchestva im. D. I. Mendeleeva,19, 294 (1974).Google Scholar
- 14.V. I. Stanko, A. N. Kashin, and I. P. Beletskaya, J. Organometal. Chem.,56, 111 (1973).Google Scholar
- 15.E. M. Kosower, in: Introduction to Physical Organic Chemistry, Wiley (1968).Google Scholar
- 16.O. B. Nagy and J. B. Nagy, Ind. Chim. Belg.,36, 829 (1971).Google Scholar
- 17.G. B. Sergeev, Zh. Vses. Khim. Obshchestva im. D. I. Mendeleeva,19, 285 (1974).Google Scholar
- 18.G. B. Sergeev, Yu. A. Serguchev, and V. V. Smirnov, Usp. Khim.,42, 1545 (1973).Google Scholar
- 19.V. F. Traven and R. West, Zh. Obshch. Khim.,44, 1834 (1974).Google Scholar
- 20.R. R. McLean, D. W. A. Sharp, and J. M. Winfield, J. Chem. Soc. Dalton Trans., 676 (1972).Google Scholar
- 21.S. Yamabe, T. Minato, J. Fujimoto, and K. Fukui, Theoret. Chim. Acta,32, 187 (1974).Google Scholar
- 22.D. S. Matteson, Organometal. Chem. Revs.,A4, 263 (1969).Google Scholar
- 23.R. S. Mulliken and W. B. Person, Molecular Complexes, Wiley, New York (1969).Google Scholar
- 24.Rupture Energies of Chemical Bonds. Ionization Potentials and Electron Affinity, Handbook [in Russian], Nauka (1974).Google Scholar
- 25.O. Yu. Okhlobystin, Electron Transfer in Organic Reactions [in Russian], Izd. Rostovsk. Univ. (1974).Google Scholar
- 26.Yu. G. Bundel, V. K. Piotrovskii, V. I. Rozenberg, and O. A. Reutov, Dokl. Akad. Nauk SSSR,207, 599 (1972).Google Scholar
- 27.V. K. Piotrovskii, V. I. Rozenberg, Yu. G. Bundel, and O. A. Reutov, Zh. Organ. Khim.,10, 1329 (1974).Google Scholar
- 28.D. V. Banthorpe, Chem. Rev.,70, 295 (1970).Google Scholar
- 29.F. R. Jensen and L. H. Gale, J. Amer. Chem. Soc.,82, 145 (1960).Google Scholar
- 30.L. G. Makarova and A. N. Nesmeyanov, Methods in Heteroorganic Chemistry. Mercury [in Russian], Nauka (1966).Google Scholar
- 31.K. A. Kocheshkov, N. N. Semlyanskii, N. I. Sheverdina, and E. M. Panov, Methods in Heteroorganic Chemistry. Germanium, Tin, and Lead [in Russian], Nauka (1968).Google Scholar
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© Plenum Publishing Corporation 1976