Summary
-
1.
The decomposition of double salts of diazonium and metal chlorides by means of metal powders with formation of organometallic compounds (the Nesmeyanov reaction) is heterolytic in character.
-
2.
The synthesis of organometallic compounds by reaction of arenediazonium chlorides with metal powders (the Waters reaction) proceeds through intermediate formation of a double salt of diazonium and metal chlorides.
Similar content being viewed by others
Literature cited
A. N. Nesmeyanov, J. Russ. Chem. Soc. 61, 1393 (1929); Ber. 62, 1010 (1929).
A. N. Nesmeyanov and E. I. Kan, J. Russ. Chem. Soc. 61, 1407 (1929); Ber. 62, 1018 (1929).
A. N. Nesmeyanov and I. T. Eskin, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1942, 116.
A. N. Nesmeyanov, N. F. Glushnev, P. F. Epifansky, and A. I. Flegontov, J. Gen. Chem. 4, 713 (1934); Ber. 67, 130 (1934).
A. N. Nesmeyanov and L. G. Makarova, J. Gen. Chem. 1, 598 (1931).
A. N. Nesmeyanov and I. F. Lutsenko, J. Gen. Chem. 11, 382 (1941).
A. N. Nesmeyanov, K. A. Kocheshkov, and V. A. Klimova, Ber. 68, 1877 (1935); K. A. Kocheshkov, A. N. Nesmeyanov, and V. A. Klimova, J. Gen. Chem. 6, 167 (1936).
A. N. Nesmeyanov and L. G. Makarova, Proc. Acad. Sci. USSR 87, 431 (1952).
N. K. Gipp, K. A. Kocheshkov, and A. N. Nesmeyanov, J. Gen. Chem. 7, 172 (1936).
A. N. Nesmeyanov, K. A. Kocheshkov and M. M. Nad, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1945, 552.
W. Waters and W. Hanby, J. Chem. Soc. 1946, 1029.
O. A. Reutov and Yu. G. Bundel, Bull. Moscow State Univ. 1955, No. 8, 85.
O. A. Reutov and Yu. G. Bundel, J. Gen. Chem. 25, 2324 (1955) (T.p. 2295).
A. N. Nesmeyanov and K. A. Kocheshkov, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1944, 416.
O. A. Reutov, Proc. Acad. Sci. USSR 87, 73 (1952).
O. A. Reutov and A. Markovskaya, Proc. Acad. Sci. USSR 98, 979 (1954).
O. A. Reutov, A. Markovskaya and A. N. Lovtsova, Proc. Acad. Sci. USSR 99, 269 (1954).
A. N. Nesmeyanov, O. A. Reutov and P. G, Knol, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1954, 410 (T.p. 347)
O. A. Reutov, Proc. Acad. Sci. USSR 87, 991 (1952).
O. A. Reutov and V. V. Kondratyeva, J. Gen. Chem. 24, 1259 (1954) (T.p. 1245).
A. N. Nesmeyanov, O. A. Reutov and O. A. Ptitsyna, Proc. Acad. Sci. USSR 91, 1341 (1953).
O. A. Reutov and A. Markovskaya, Proc. Acad. Sci. USSR 99, 543 (1954).
T. K. Kozminskaya, M. M. Nad and K. A. Kocheshkov, J. Gen. Chem. 16, 891 (1946).
A. N. Nesmeyanov and L. G. Makarova, Proc. Acad. Sci. USSR 87, 417 (1952).
W. A. Waters, Chemistry of Free Radicals (Oxford, 1946) (Foreign Lit. Press, Moscow, 1948), p. 178.
A. Markovskaya, Thesis, Synthesis of Mixed Organoantimony Compounds via Diazo Compounds (Moscow, 1955).
O. A. Reutov, A. Markovskaya and R. E. Mardaleishvili, Proc. Acad. Sci. USSR 104, 253 (1955).
D. H. Hey, Quart. Revs. 8, 308 (1954).
O. A. Reutov and O. A. Ptitsyna, Proc. Acad. Sci. USSR 102, 291 (1955).
A. N. Nesmeyanov, Sci. Mem. Moscow State Univ, 1934, No. 3, 291.
R. McClure and A. Lowry, J. Am. Chem. Soc. 53, 319 (1931).
Brit. Pat. 638565, C. A. 44, 9478 f (1950).
F. Makin and W. Waters, J. Am. Chem. Soc. 53, 319 (1931).
Author information
Authors and Affiliations
Additional information
Communication from A. N. Nesmeyanov's department.
Rights and permissions
About this article
Cite this article
Reutov, O.A. Mechanism of reactions between diazo compounds and metals with formation of organometallic compounds. Russ Chem Bull 5, 963–970 (1956). https://doi.org/10.1007/BF01166411
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01166411