Summary
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1.
The reaction of asymmetric organomercury compounds with carbon tetrachloride proceeds via a radical mechanism in the presence of benzoyl peroxide. The less reactive group linked to mercury in RHgR' stays attached to mercury, but the more reactive group is converted into RCCl3.
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2.
A series has been established for radicals arranged in order of decreasing affinity towards the free radical CC13.
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Literature cited
C. S. Marvel, H. A. Calvery, J. Amer. Chem. Soc.45, 820 (1923).
A. H. Corwin, M. A. Naylor, J. Amer. Chem. Soc.69, 1004 (1947).
F. Nerdel, S. Makover, Naturwissenschaften20, 490 (1958).
R. E. Dessy, G. F. Reynolds, Jin Young-Kim, J. Amer. Chem. Soc.81, 2683 (1959).
S. Winstein, T. G. Traylor, J. Amer. Chem. Soc.77, 3741 (1955).
M. S. Kharasch, R. Marker, J. Amer. Chem. Soc.48, 3130 (1926); M. S. Kharasch, M. W. Grafflin, J. Amer. Chem. Soc.47, 1948 (1925); M. S. Kharasch, A. L. Flenner, J. Amer. Chem. Soc.54, 674 (1932).
A. N. Nesmeyanov and K. A. Kocheshkov, Uch. Zap. MGU, No. 3, 283 (1934).
A. E. Borisov, Izv. AN SSSR, Otd. khim. 524 (1951).
R. Kh. Freidlina, K. A. Kocheskov, and A. N. Nesmeyanov, Zh. Obshch. Khimii,5, 1171 (1935)
A. Michoelis, U. Genzken, Liebigs. Ann. Chem.242, 185 (1887).
N. V. Sidgwick, N. J. Spurrell, T. L. Davies, J. Chem. Soc.107, 1207 (1915).
V. S. Kidinova, Dissertation, Alma-Ata, 1953.
M. M. Koton, Zh. Obshch. Khimii,9, 912 (1939).
R. Otto, J. Prakt. Chem. [2],1, 185 (1870).
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Nesmeyanov, A.N., Borisov, A.E., Golubeva, E.I. et al. The reaction of free radicals with asymmetric organomercury compounds. Russ Chem Bull 10, 1477–1482 (1961). https://doi.org/10.1007/BF00906136
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DOI: https://doi.org/10.1007/BF00906136