Home / Articles / Free radical reactions in the electrolysis of organic compounds

Free radical reactions in the electrolysis of organic compounds

Andrei Petrovich Tomilov 1
Andrei Petrovich Tomilov
, 
Mikhail Yakovlevich Fioshin 1
Mikhail Yakovlevich Fioshin
1 Institute of Electrochemistry of the USSR Academy of Sciences, Moscow
10.1070/RC1963v032n01ABEH001291
Published 30 November 1962
Communication , Volume 32, Issue 1, 30-44
13
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Tomilov A. P., Fioshin M. Y. Free radical reactions in the electrolysis of organic compounds // Russian Chemical Reviews. 1963. Vol. 32. No. 1. pp. 30-44.
GOST all authors (up to 50)
Copy cite
Tomilov A. P., Fioshin M. Y. Free radical reactions in the electrolysis of organic compounds // Russian Chemical Reviews. 1963. Vol. 32. No. 1. pp. 30-44.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RC1963v032n01ABEH001291
UR - https://rcr.colab.ws/publications/10.1070/RC1963v032n01ABEH001291
TI - Free radical reactions in the electrolysis of organic compounds
T2 - Russian Chemical Reviews
AU - Tomilov, Andrei Petrovich
AU - Fioshin, Mikhail Yakovlevich
PY - 1963
DA - 1962/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 30-44
IS - 1
VL - 32
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{1963_Tomilov,
author = {Andrei Petrovich Tomilov and Mikhail Yakovlevich Fioshin},
title = {Free radical reactions in the electrolysis of organic compounds},
journal = {Russian Chemical Reviews},
year = {1963},
volume = {32},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1963v032n01ABEH001291},
number = {1},
pages = {30--44},
doi = {10.1070/RC1963v032n01ABEH001291}
}
MLA
Cite this
MLA
Copy cite
Tomilov, Andrei Petrovich, and Mikhail Yakovlevich Fioshin. “Free radical reactions in the electrolysis of organic compounds.” Russian Chemical Reviews, vol. 32, no. 1, Nov. 1963, pp. 30-44. https://rcr.colab.ws/publications/10.1070/RC1963v032n01ABEH001291.
Views / Visits / Downloads
12 / 12 / 2

Abstract

CONTENTS
I. Introduction 30
II. Methods of detecting free radicals in the electrolysis of organic compounds 30
III. Classification of electrochemical reactions leading to the formation of free radicals 33
IV. Free radical reactions 34
V. Behaviour of free radicals formed during electrolysis 41

References

2.
Kurzlebige Radikale als Zwischenprodukte
Goldschmidt S.
Angewandte Chemie , 1957
3.
Syntheses by Free-radical Reactions. X. Electrochemical Additive Dimerizations
Lindsey R.V., Peterson M.L.
Journal of the American Chemical Society , 1959
4.
4
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
5.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1953
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
7.
Polarographic Studies in Acetonitrile and Dimethylformamide II . Behavior of Aromatic Olefins and Hydrocarbons
Wawzonek S., Blaha E.W., Behkey R., Runner M.E.
Journal of the Electrochemical Society , 2007
9.
Reaction of Sodium Metal with Aromatic Hydrocarbons1,2
Paul D.E., Lipkin D., Weissman S.I.
Journal of the American Chemical Society , 1956
10.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959
11.
11
T. T. Bannister
Diss. Abstr. , 1959
14.
14
V. B. Evstigneev
Zhur. Fiz. Khim. , 1958
16.
Mechanism of the Electrochemical Reduction of Phenyl Ketones
Elving P.J., Leone J.T.
Journal of the American Chemical Society , 1958
18.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
19.
Potentiometric and Magnetometric Study of the Duroquinone System
Michaelis L., Schubert M.P., Reber R.K., Kuck J.A., Granick S.
Journal of the American Chemical Society , 1938
20.
20
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
22.
The Theory of Reversible Two-step Oxidation Involving Free Radicals.
Michaelis L., Schubert M.P.
Chemical Reviews , 1938
23.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR , 1958
24.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR , 1951
25.
FORMATION OF STABLE FREE RADICALS ON ELECTROREDUCTION OF N-ALKYLPYRIDINIUM SALTS
Schwarz W.M., Kosower E.M., Shain I.
Journal of the American Chemical Society , 1961
26.
26
B. Ya. Dain
1957
30.
Electrochemical method of studying the reactions of free ketyl radicals
Kemula W., Grabowski Z.R., Kalinowski M.K.
Die Naturwissenschaften , 1960
32.
Informal Discussion of Electroanalytical Chemistry
Reinmuth W.H., Reilley C.N., Rogers L.B.
Analytical Chemistry , 1959
36.
36
J. Billon
Bull. Soc. chim. France , 1960
37.
Electron Spin Resonance Study ofp‐Phenylene‐Diamine Positive Ion
Melchior M.T., Maki A.H.
Journal of Chemical Physics , 1961
38.
ELECTROLYTIC GENERATION OF RADICAL IONS IN AQUEOUS SOLUTION
Piette L.H., Ludwig P., Adams R.N.
Journal of the American Chemical Society , 1961
39.
The Free Radicals of the Type of Wurster's Salts
Michaelis L., Schubert M.P., Granick S.
Journal of the American Chemical Society , 1939
40.
Voltammetry at Solid Electrodes
Parker R.E., Adams R.N.
Analytical Chemistry , 1956
41.
TERNARY INTERMETALLIC COMPOUNDS
Vul'f B.K.
Russian Chemical Reviews , 1960
42.
ELECTROLYTIC CONDENSATION OF CARBOXYLIC ACIDS
Svadkovskaya G.E., Voitkevich S.A.
Russian Chemical Reviews , 1960
43.
43
N. Bunge
Ber. Deutsch. Chem. Ges. , 1870
44.
Elektrolyse von Kaliumxanthogenat in wässriger Lösung
Schall C.
Berichte der Bunsengesellschaft für physikalische Chemie , 1896
46.
Apparate für wissenschaftliche Untersuchungen
Berichte der Bunsengesellschaft für physikalische Chemie , 1898
47.
The Ionic Nature of the Grignard Reagent
Evans W.V., Pearson R.
Journal of the American Chemical Society , 1942
48.
48
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
49.
49
A. A. Krasnovskii
Biofizika , 1958
50.
50
G. Glacomello
Gazzetta. , 1935
51.
Ueber die Electrolyse einiger chemischen Verbindungen
Bunge N.
Berichte der deutschen chemischen Gesellschaft , 1870
52.
52
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
53.
53
D. Porretand E. Rabinowitch
Nature , 1937
54.
54
R. Livingston
J. Phys. Chem. , 1941
55.
55
G. A. Bogdanovskii
1958
56.
56
T. Iasui
Bull. Chem. Soc. Japan. , 1935
57.
57
R. Livingston
"Research in Photosynthesis" , 1957
58.
58
N. E. Khomutov
1953
59.
59
H. Linshitz
"Research in Photosynthesis" , 1957
60.
60
A. N. Terenin
Optika i Spektrosk. , 1956
61.
ANODIC SUBSTITUTION REACTIONS
Tomilov A.P.
Russian Chemical Reviews , 1961
62.
Elektrochemische Chlorierung von Benzol und Toluol
Fichter F., Glantzstein L.
Berichte der deutschen chemischen Gesellschaft , 1916
63.
63
1930
64.
64
Chem. Zentr. II , 1931
65.
Über elektrochemische Rhodanierung aromatischer Amine und Phenole
Fichter F., Schönmann P.
Helvetica Chimica Acta , 1936
66.
66
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
67.
67
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1940
68.
68
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1946
69.
69
B. Commoner
1958
70.
70
N. Bubnov
Biofizika , 1960
71.
The Electrochemical Degradation of Quaternary Ammonium Salts1
Finkelstein M., Petersen R.C., Ross S.D.
Journal of the American Chemical Society , 1959
72.
A Study of Reaction Products and Mechanism in the Electrolytic Reduction of Ethyl Iodide
Plump R.E., Hammett L.P.
Transactions of The Electrochemical Society , 2011
74.
74
F. F. Litvin
Uspekhi Fiz. Nauk , 1960
75.
Über 1.1.4.4‐Tetraaryl‐butin‐2. (6. Mitteilung über die Reduktion organischer Halogenverbindungen)
Brand K.
Berichte der deutschen chemischen Gesellschaft (A and B Series) , 1921
77.
77
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
78.
78
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
80.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1937
81.
81
J. C. Ghosh
J. Indian Chem. Soc. , 1934
82.
A NEW METALLO-ORGANIC COMPOUND: DIPLUMBIC HEXAETHYL1
Midgley T., Hochwalt C.A., Calingaert G.
Journal of the American Chemical Society , 1923
83.
Eine verbesserte Darstellung von Triäthylblei und Trimethylblei
Hein F., Klein A.
Berichte der deutschen chemischen Gesellschaft (A and B Series) , 1938
84.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
85.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
86.
The polarographic reduction of conjugated hydrocarbons: II. The reduction of 1,n-diphenylpolyenes
Hoijtink G.J., van Schooten J.
Recueil des Travaux Chimiques des Pays-Bas , 2010
87.
The polarographic reduction of conjugated hydrocarbons: IV. The mechanism of the reduction of various alternant and non‐alternant hydrocarbons
Hoijtink G.J., van Schooten J., de Boer E., Aalbersberg W.I.
Recueil des Travaux Chimiques des Pays-Bas , 2010
88.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1946
89.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow , 1955
90.
Electrolytic Reduction of Acetone
Wilson C.L., Wilson K.B.
Transactions of The Electrochemical Society , 2011
91.
The Kinetics of the Electroreduction of Acetone
Hennig G.R., Kimball G.E.
Journal of Chemical Physics , 1944
92.
92
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
93.
93
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
95.
95
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
97.
Die Elektrolyse der Indan-carbonsäure-(2)
Fichter F., Stenzl H.
Helvetica Chimica Acta , 1939
98.
The Electrolysis of Some Higher Aliphatic Organomagnesium Halides in Ethyl Ether
Evans W.V., Braithwaite D., Field E.
Journal of the American Chemical Society , 1940
99.
99
V. V. Zolotarev
1938
100.
100
V. V. Zolotarev
Chem. Abs. , 1941
101.
Neue Bücher
Berichte der Bunsengesellschaft für physikalische Chemie , 1901
102.
102
F. Fichter
Helv. Chim. Acta , 1922
103.
Die elektrochemische Oxydation der Benzolhomologen. I. m-Xylol
Fichter F., Meyer J.
Helvetica Chimica Acta , 1925
104.
Elektrochemische Oxydation des ?-Methyl-naphtalins
Fichter F., Herszbein S.
Helvetica Chimica Acta , 1928
105.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR , 1958
106.
106
F. Fichter
Helv. Chim. Acta , 1927
108.
108
F. Fichter
Helv. Chim. Acta , 1924
109.
109
F. Ficher
Bull. Soc. chim. France (4) , 1916
110.
Über Cyan‐cyclaminane)
Kaufmann A., Albertini A.
Berichte der deutschen chemischen Gesellschaft , 1909
111.
111
M. Calvin
1956
112.
112
A. G. Pozdeeva
Zhur. Prikl. Khim. , 1952
113.
�ber polarographische Untersuchungen von Cumarinen. II
Patzak R., Neugebauer L.
Monatshefte fur Chemie , 1952
114.
Über die Bildung von Dipiperidylen bei der elektrolytischen Reduktion von Pyridin
Emmert B.
Berichte der deutschen chemischen Gesellschaft , 1913
115.
115
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1957
116.
Elektrosynthesen in der Pyridin- und Chinolinreihe
Ahrens F.B.
Berichte der Bunsengesellschaft für physikalische Chemie , 1896
117.
117
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
118.
118
V. M. Rodionov
Zhur. Obshch. Khim. , 1935
119.
119
V. V. Levchenko
Zhur. Obshch. Khim. , 1947
120.
120
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
123.
123
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
124.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
125.
CLXVI.—Electrolytic reduction. Part VII. The catalytic action of copper
Law H.D.
Journal of the Chemical Society Transactions , 1912
126.
126
J. Wiemannand Ch. Clachet
Compt. rend. , 1948
127.
127
R. Pasternak
Helv. Chim. Acta , 1948
128.
128
J. Wiemann
Bull. Soc. chim. France , 1952
129.
129
J. Wiemann
Bull. Soc. chim. France , 1955
130.
130
J. Wiemann
Bull. Soc. chim. France , 1958
131.
131
N. Thooi
Compt. rend. , 1958
132.
132
G. Shima
Kyoto Univ. , 1929
133.
133
C. Wilson
Trans. Electrochem. Soc. , 1941
134.
Analogies between Electrolytic and Chemical Methods of Reduction
Wilson C.L.
Transactions of The Electrochemical Society , 2011
135.
187. Electrolytic reduction of organic compounds. Part III. β-Vinylacrylic acid
Isaacs E., Wilson C.L.
Journal of the Chemical Society (Resumed) , 1936
136.
Electrolytic Reduction of Cinnamic Acid
Wilson C.L.
Transactions of The Electrochemical Society , 2011
137.
Electrolytic Reduction of Cinnamic Acid
Wilson C.L., Wilson K.B.
Transactions of The Electrochemical Society , 2011
138.
138
S. Ono
J. Chem. Soc. Japan , 1957
139.
139
I. L. Knunyants
1959
140.
140
1912
141.
141
Friedl.
142.
142
1913
143.
143
Friedl.
144.
144
1912
145.
145
Friedl.
146.
Elektrolytische Reduktion des Benzaldehyds
Kauffmann H.
Berichte der Bunsengesellschaft für physikalische Chemie , 1895
147.
147
Y. Sasada
Acta Cryst. , 1898
150.
CXLIX.—Electrolytic reduction. I. Aromatic aldehydes
Law H.D.
Journal of the Chemical Society Transactions , 1906
151.
151
V. M. Rodionov
Zhur. Obshch. Khim. , 1936
152.
152
W. Albert
Trans. Electrochem. Soc. , 1943
153.
153
1899
154.
154
Friedl.
155.
Über die elektrochemische Reduktion von Ketonen
Elbs K., Brand K.
Berichte der Bunsengesellschaft für physikalische Chemie , 1902
156.
Leitfähigkeit
Berichte der Bunsengesellschaft für physikalische Chemie , 1902
157.
157
1903
158.
158
Friedl.
159.
159
J. Tafel
Z. Elektrochem. , 1911
160.
160
1912
161.
161
Friedl.
162.
162
1917
163.
163
Friedl.
164.
164
1917
165.
165
Friedl.
166.
166
1917
167.
167
Friedl.
168.
168
1918
169.
169
Friedl.
170.
170
1918
171.
171
Friedl.
172.
172
1918
173.
173
Friedl.
174.
174
S. Calvert
India Rubber Tire Rev. , 1926
176.
177
J. Henry
Proc. R. Irish Acad. , 1945
177.
178
1946
178.
179
Chem. Abs. , 1947
179.
180
1946
180.
181
Chem. Abs. , 1947
181.
182
1947
182.
183
Chem. Abs. , 1947
183.
Electrolytic Reduction of Acetone to Pinacol
Slotterbeck O.C.
Transactions of The Electrochemical Society , 2011
184.
185
1954
185.
186
Chem. Abs. , 1956
186.
187
1954
187.
188
Chem. Abs. , 1955
188.
189
M. Godchot
Bull. Soc. chim. France (5) , 1913
189.
190
H. Law
J. Chem. Soc. , 1912
190.
191
M. Matsui
Mem. Coll. Sci., Kyoto Univ. , 1920
191.
192
E. Pannain
Rend. Classe Sci. fis. mat. nat. (5) , 1908
192.
193
E. Pannain
Gazzetta , 1909
193.
The Synthesis of Some Pyridyl Glycols by Electrolytic Reduction
Allen M.J., Cohen H.
Journal of the Electrochemical Society , 2007
194.
195
M. Allen
J. Chem. Soc. , 1961
195.
196
E. Müller
Z. Elektrochem. , 1910
196.
Über die elektrochemische Reduktion von Ketonen
Riesenfeid E.H.
Berichte der Bunsengesellschaft für physikalische Chemie , 1901
197.
198
W. Cohen
Rec. Trav. chim. , 1919
198.
The Influence of Iron Salts on the Electrolytic Reduction of Benzophenone
Swann S.
Transactions of The Electrochemical Society , 2011
199.
The Electrolytic Reduction of Ketones in Glacial Acetic Acid
Swann S.
Transactions of The Electrochemical Society , 2011
200.
The Electrolytic Reduction of Benzophenone in Acidic and in Alkaline Media
Swann S., Briggs S.W., Neklutin V.C., Jerome A.J.
Transactions of The Electrochemical Society , 2011
201.
202
G. Shiroa
Mem. Coll. Sci., Kyoto Univ. , 1930
203.
Elektrolyse der Alkalisalze der organischen Säuren
Petersen J.
Zeitschrift fur Physikalische Chemie , 1900
204.
205
N. Bunge
Zhur. Russ. Fiz.-Khim. Obshch. , 1889
205.
206
J. Petersen
Z. Phys. Chem. , 1900
206.
207
F. Fichter
"Organische Elektrochemie" , 1942
207.
208
O. A. Reutov
"Teoreticheskie Problemy Organicheskoi Khimii" (Theoretical Problems in Organic Chemistry) , 1956
208.
209
C. J. Haggerty
Trans. Am. Electrochem. Soc. , 1929
209.
Eine merkwürdige Bildungsweise von Quecksilberalkylen
Tafel J.
Berichte der deutschen chemischen Gesellschaft , 1906
210.
211
C. Schall
Z. Elektrochem. , 1923
211.
Ungesättigte Bleialkyle
Tafel J.
Berichte der deutschen chemischen Gesellschaft , 1911
212.
Bleialkylverbindungen aus Methyläthyl‐keton und Diäthylketon
Renger G.
Berichte der deutschen chemischen Gesellschaft , 1911
214.
Elektrolytische Reduktion von Aldehyden
Schepss W.
Berichte der deutschen chemischen Gesellschaft , 1913
215.
216
A. P. Tomilov
Zhur. Prikl. Khim. , 1959
216.
217
1925
217.
218
Chem. Zentr. II , 1925
218.
Über das salzartige Verhalten der Alkalialkyle in Metallalkylen als Lösungsmitteln
Hein F., Petzchner E., Wagler K., Segitz F.A.
Zeitschrift fur Anorganische und Allgemeine Chemie , 1924
219.
220
K. Ziegler
Angew. Chem. , 1955
220.
221
1960
221.
222
Chem. Abs. , 1961
222.
223
1959
223.
224
Chem. Abs. , 1959
224.
225
1960
225.
226
Chem. Abs. , 1961
226.
227
B. Roetheke
1958
227.
228
B. Roetheke
Chem. Abs. , 1959
228.
229
1959
229.
230
Chem. Abs. , 1962
230.
231
1960
231.
232
Chem. Abs. , 1960
232.
Über die elektrolytische Darstellung der Alkoholate und der Alkoholat‐Carbonsäureester
Sailäard B.
Berichte der Bunsengesellschaft für physikalische Chemie , 1906
234.
Electrolysis of Methylmagnesium Halides in Ether Solutions
Evans W.V., Field E.
Journal of the American Chemical Society , 1936
235.
Electrolysis of Methylmagnesium Iodide in n-Butyl Ether
Evans W.V., Field E.
Journal of the American Chemical Society , 1936
236.
The Electrolysis of n-Propylmagnesium Bromide and Isopropylmagnesium Bromide in Ethyl Ether
Evans W.V., Braithwaite D.
Journal of the American Chemical Society , 1939
237.
The Electrolysis of Arylmagnesium Bromides in Ethyl Ether: the Behavior of Shortlived Aryl Free Radicals
Evans W.V., Pearson R., Braithwaite D.
Journal of the American Chemical Society , 1941
238.
Methylation of Aromatic Nitro Compounds with Lead Tetraacetate
Fieser L.F., Clapp R.C., Daudt W.H.
Journal of the American Chemical Society , 1942
239.
240
W. A. Waters
"The Chemistry of Free Radicals" , 1948
240.
241
M. S. Kharasch
"Grignard Reactions of Nonmetallic Substances" , 1954
241.
242
N. N. Seroenov
"O Nekotorykh Problemakh Khimicheskoi Kinetiki i Reaktsionnoi Sposobnosti" (Some Problems in Chemical Kinetics and Reactivity) , 1958
242.
INITIATION OF STYRENE POLYMERIZATION AT A CATHODE
Yang J.Y., McEwen W.E., Kleinberg J.
Journal of the American Chemical Society , 1957
243.
244
C. Wilson
Record. Chem. Prog. , 1949
245.
Polymerization Induced by Hydrogen in Metals*
Parravano G.
Journal of the American Chemical Society , 1951
246.
Electrolytic Reduction of Organic Compounds
Dineen E., Schwan T.C., Wilson C.L.
Journal of the Electrochemical Society , 2007
247.
248
M. Ya. Fioshin
Plasticheskie Massy , 1960
248.
249
A. I. Fedorova
Dokl. Akad. Nauk SSSR , 1961
249.
250
D. Goerrig
1955
250.
251
D. Goerrig
Chem. Abs. , 1959
251.
252
D. Goerrig
1956
252.
253
D. Goerrig
Chem. Abs. , 1959
255.
Syntheses by Free-radical Reactions. II. Additive Dimerizations Effected by Hydroxyl Radicals
Coffman D.D., Jenner E.L.
Journal of the American Chemical Society , 1958