Home / Articles / Reactions of adamantanes in electrophilic media

Reactions of adamantanes in electrophilic media

Igor Konstantinovich Moiseev 1
Igor Konstantinovich Moiseev
, 
Nadezhda Viktorovna Makarova 1
Nadezhda Viktorovna Makarova
, 
Margarita Nikolaevna Zemtsova 1
Margarita Nikolaevna Zemtsova
1 Samara State Technical University
10.1070/RC1999v068n12ABEH000495
Published 30 November 1998
Communication , Volume 68, Issue 12, 1001-1020
42
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Moiseev I. K., Makarova N. V., Zemtsova M. N. Reactions of adamantanes in electrophilic media // Russian Chemical Reviews. 1999. Vol. 68. No. 12. pp. 1001-1020.
GOST all authors (up to 50)
Copy cite
Moiseev I. K., Makarova N. V., Zemtsova M. N. Reactions of adamantanes in electrophilic media // Russian Chemical Reviews. 1999. Vol. 68. No. 12. pp. 1001-1020.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RC1999v068n12ABEH000495
UR - https://rcr.colab.ws/publications/10.1070/RC1999v068n12ABEH000495
TI - Reactions of adamantanes in electrophilic media
T2 - Russian Chemical Reviews
AU - Moiseev, Igor Konstantinovich
AU - Makarova, Nadezhda Viktorovna
AU - Zemtsova, Margarita Nikolaevna
PY - 1999
DA - 1998/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 1001-1020
IS - 12
VL - 68
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{1999_Moiseev,
author = {Igor Konstantinovich Moiseev and Nadezhda Viktorovna Makarova and Margarita Nikolaevna Zemtsova},
title = {Reactions of adamantanes in electrophilic media},
journal = {Russian Chemical Reviews},
year = {1999},
volume = {68},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1999v068n12ABEH000495},
number = {12},
pages = {1001--1020},
doi = {10.1070/RC1999v068n12ABEH000495}
}
MLA
Cite this
MLA
Copy cite
Moiseev, Igor Konstantinovich, et al. “Reactions of adamantanes in electrophilic media.” Russian Chemical Reviews, vol. 68, no. 12, Nov. 1999, pp. 1001-1020. https://rcr.colab.ws/publications/10.1070/RC1999v068n12ABEH000495.
Views / Visits / Downloads
12 / 12 / 3

Abstract

Published data on the synthesis of adamantane derivatives bearing various functional groups (halogen, hydroxy, nitrato, amino, carboxy and others) are systematised and generalised. The bibliography includes 236 references.

References

1.
Advances in the Chemistry of Adamantane
Sevost'yanova V.V., Krayushkin M.M., Yurchenko A.G.
Russian Chemical Reviews , 1970
2.
Advances in the Synthesis of Heteroadamantanes
Averina N.V., Zefirov N.S.
Russian Chemical Reviews , 1976
3.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1953
4.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
5.
7
E. Rabinowitch
"Photosynthesis" , 1956
6.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) , 1959
7.
9
V. H. Lynch
Carnegie Inst. Year Book , 1954
8.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959
9.
Polymeric Derivatives of Adamantane
Khardin A.P., Radchenko S.S.
Russian Chemical Reviews , 1982
10.
13
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
11.
14
V. B. Evstigneev
Zhur. Fiz. Khim. , 1958
12.
15
A. S. Holt
"Research in Photosynthesis" , 1957
13.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
14.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
15.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
21.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR , 1951
22.
25
G. W. Robinson
J. Chem. Phys. , 1955
23.
26
B. Ya. Dain
1957
24.
27
A. A. Krasnovskii
Biofizika , 1956
25.
28
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
26.
29
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
27.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
28.
31
A. A. Krasnovskii
Biokhimiya , 1960
29.
32
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
30.
On the mechanism of liquid phase halogenation of adamantane derivatives
Yurchenco A.G., Kulik N.I., Kuchar V.P., Djakovskaja V.M., Baklan V.F.
Tetrahedron Letters , 1986
31.
34
G. W. Robinson
J. Chem. Phys. , 1886
32.
Stable Carbonium Ions. VIII. The 1-Adamantyl Cation
Schleyer P.V., Fort R.C., Watts W.E., Comisarow M.B., Olah G.A.
Journal of the American Chemical Society , 1964
33.
36
J. Billon
Bull. Soc. chim. France , 1960
34.
37
L. M. Kosobutskaya
Dokl. Akad. Nauk SSSR , 1950
35.
Mechanism of the oxidation of alkanes with nitronium tetrafluoroborate in acetonitrile. Evidence for a carbenium ion intermediate
Bach R.D., Holubka J.W., Badger R.C., Rajan S.J.
Journal of the American Chemical Society , 1979
36.
39
V. F. Gachkovskii
Biofizika , 1959
38.
Competitive substitution and fragmentation reactions of cation radicals derived from adamantanes
Edwards G.J., Jones S.R., Mellor J.M.
Journal of the Chemical Society Chemical Communications , 1975
39.
Oxidative decomposition of 1,1'-azoadamantane by thianthrene cation radical. Carbocationic chemistry from a free radical source
Bae D.H., Engel P.S., Hoque A.K., Keys D.E., Lee W.K., Shaw R.W., Shine H.J.
Journal of the American Chemical Society , 1985
42.
45
W. Hendrich
Roczniki Chemii , 1958
44.
Fluorination of 1,4-dioxan with sulfur tetrafluoride in hydrogen fluoride
Kunshenko B.V., Muratov N.N., Burmakov A.I., Alexeeva L.A., Yagupolskii L.M.
Journal of Fluorine Chemistry , 1983
45.
Synthesis of perfluoroalkyladamantanes
Moore R.E., Driscoll G.L.
Journal of Organic Chemistry , 1978
46.
49
A. A. Krasnovskii
Biofizika , 1958
47.
50
G. Glacomello
Gazzetta. , 1935
48.
51
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
49.
52
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
50.
53
D. Porretand E. Rabinowitch
Nature , 1937
51.
54
R. Livingston
J. Phys. Chem. , 1941
54.
57
R. Livingston
"Research in Photosynthesis" , 1957
55.
58
N. E. Khomutov
1953
56.
59
H. Linshitz
"Research in Photosynthesis" , 1957
57.
60
A. N. Terenin
Optika i Spektrosk. , 1956
58.
61
A. N. Terenin
1959
59.
62
A. A. Krasnovskii
"Sbornik, Voprosy Khimicheskoi Kinetiki" (Symposium, Problems of Chemical Kinetics) , 1955
60.
63
1930
61.
Neue Möglichkeiten der Direktsubstitution am Adamantan
Stetter H., Krause M., Last W.-.
Angewandte Chemie , 1968
64.
Chlorination of adamantane by ferric chloride and antimony pentachloride
Kovacic P., Chang J.C.
Journal of the Chemical Society D Chemical Communications , 1970
66.
The Reactivity of Bridgehead Compounds of Adamantane1,2
von R. Schleyer P., Nicholas R.D.
Journal of the American Chemical Society , 1961
67.
70
N. Bubnov
Biofizika , 1960
68.
71
Yu. A. Shlyapnikov
Vysokomol. Soed. , 1962
70.
Dibromination of Adamantane1
Baughman G.L.
Journal of Organic Chemistry , 1964
71.
74
F. F. Litvin
Uspekhi Fiz. Nauk , 1960
72.
75
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
73.
76
A. N. Terenin
"Fotokhimiya Krasitelei" (The Photochemistry of Dyes) , 1947
74.
Some Reactions of Adamantane and Adamantane Derivatives
SMITH G.W., WILLIAMS H.D.
Journal of Organic Chemistry , 1961
75.
78
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
76.
79
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
77.
Über eine neue, ergiebigere Darstellung des Adamantans
Prelog V., Seiwerth R.
Berichte der deutschen chemischen Gesellschaft (A and B Series) , 1941
79.
82
G. P. Brin
Biokhimiya , 1957
80.
83
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
83.
Bridgehead Fluorine Derivatives of Adamantane
BHANDARI K.S., PINCOCK R.E.
Synthesis , 1974
84.
Efficient conversion of alkyl chlorides into bromides
Yoon K.B., Kochi J.K.
Journal of the Chemical Society Chemical Communications , 1987
85.
Bridgehead halogen exchanges
McKinley J.W., Pincock R.E., Scott W.B.
Journal of the American Chemical Society , 1973
87.
90
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1951
88.
91
L. M. Vorob'eva
Biokhimiya , 1956
89.
Hydride transfer reactions of substituted adamantyl cations
Cuddy B.D., Grant D., Karim A., McKervey M.A., Rea E.J.
Journal of the Chemical Society Perkin Transactions 1 , 1972
90.
93
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
91.
94
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
92.
95
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
93.
96
L. M. Vorob'eva
Biokhimiya , 1958
96.
Synthetic methods and reactions. 112. Synthetic transformations with trichloromethylsilane/sodium iodide reagent
Olah G.A., Husain A., Singh B.P., Mehrotra A.K.
Journal of Organic Chemistry , 1983
97.
Brominolysis of bridgehead-substituted adamantane derivatives
Peterson M.R., Wahl G.H.
Chemical Communications (London) , 1968
98.
101
M. F. Shostakovskii
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
99.
102
F. Fichter
Helv. Chim. Acta , 1922
100.
103
L. N. Bell
Dokl. Akad. Nauk SSSR , 1956
101.
104
O. P. Osipova
Dokl. Akad. Nauk SSSR , 1950
102.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR , 1958
103.
106
F. Fichter
Helv. Chim. Acta , 1927
104.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. , 1961
105.
108
F. Fichter
Helv. Chim. Acta , 1924
106.
109
F. Ficher
Bull. Soc. chim. France (4) , 1916
107.
110
M. F. Shostakovskii
Dokl. Akad. Nauk SSSR , 1960
108.
111
M. Calvin
1956
109.
112
A. G. Pozdeeva
Zhur. Prikl. Khim. , 1952
110.
113
H. Blum
"Photodynamic Action and Diseases caused Light" , 1940
111.
114
L. Segal
"Chemical Reactions of Polymers" , 1964
112.
The Adamantyl Group in Medicinal Agents. I. Hypoglycemic N-Arylsulfonyl-N'-adamantylureas
Gerzon K., Krumkalns E.V., Brindle R.L., Marshall F.J., Root M.A.
Journal of Medicinal Chemistry , 1963
114.
Die Synthese von 1,3-disubstituierten Adamantanen
Fischer W., Grob C.A., Katayama H.
Helvetica Chimica Acta , 1976
116.
Rearrangements in the adamantane series
Raber D.J., Fort R.C., Wiskott E., Woodworth C.W., Schleyer P.V., Weber J., Stetter H.
Tetrahedron , 1971
117.
120
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
118.
121
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
119.
122
S. R. Rafikov
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
120.
Unusual behaviour of 2-methyladamantane during bromination
Alford J.R., Grant D., McKervey M.A.
Journal of the Chemical Society C Organic , 1971
121.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
122.
Bridgehead Adamantane Carbonium Ion Reactivities
Fort R.C., Schleyer P.V.
Journal of the American Chemical Society , 1964
123.
126
J. Wiemannand Ch. Clachet
Compt. rend. , 1948
124.
127
R. Pasternak
Helv. Chim. Acta , 1948
125.
128
J. Wiemann
Bull. Soc. chim. France , 1952
127.
130
J. Wiemann
Bull. Soc. chim. France , 1958
129.
132
G. Shima
Kyoto Univ. , 1929
130.
133
C. Wilson
Trans. Electrochem. Soc. , 1941
131.
134
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1948
134.
137
S. R. Rafikov
Zh. Obshch. Khim. , 1944
135.
138
S. Ono
J. Chem. Soc. Japan , 1957
136.
139
I. L. Knunyants
1959
137.
140
1912
138.
141
Friedl.
139.
142
1913
140.
143
Friedl.
141.
144
1912
142.
145
Friedl.
143.
146
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1952
145.
148
P. Kresse
Chem. Abs. , 1960
146.
149
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1954
147.
150
Ya. E. Bernadskaya
"Iskusstvennoe Volokno" (Artificial Fibres) , 1952
148.
151
V. M. Rodionov
Zhur. Obshch. Khim. , 1936
149.
152
W. Albert
Trans. Electrochem. Soc. , 1943
150.
153
1899
151.
154
Friedl.
152.
Adamantane rearrangements. The behaviour of 2-methyl-2-adamantanol in concentrated sulphuric acid
McKervey M.A., Alford J.R., McGarrity J.F., Rea E.J.
Tetrahedron Letters , 1968
153.
156
J. S. Fruton
J. Biol. Med. , 1950
154.
157
1903
155.
158
Friedl.
156.
The Adamantyl Group in Medicinal Agents. IV. Sedative Action of 3,5,7-Trimethyladamantane-1-carboxamide1 and Related Agents
Gerzon K., Tobias D.J., Holmes R.E., Rathbun R.E., Kattau R.W.
Journal of Medicinal Chemistry , 1967
157.
160
1912
158.
161
Friedl.
159.
Deamination of 1-adamantylamine
Sabo J., Hiti J., Fort R.C.
Journal of Organic Chemistry , 1974
160.
The fate of the isobutyldiazonium ion
Bayless J.H., Jurewicz A.T., Friedman L.
Journal of the American Chemical Society , 1968
161.
164
1917
162.
165
Friedl.
163.
166
1917
164.
167
Friedl.
165.
168
1918
168.
Direkte Synthese der Adamantan-carbonsäure-(1)
Koch H., Haaf W.
Angewandte Chemie , 1960
169.
Synthesis of 13C—O-labelled tertiary alkanoic acids by the Koch-haaf-reaction
Langhals H., Mergelsberg I., Rüchardt C.
Tetrahedron Letters , 1981
170.
173
Friedl.
171.
174
S. Calvert
India Rubber Tire Rev. , 1926
172.
175
I. Mayer
1966
173.
176
G. V. Samsonov
"Metody Ispytaniya na Mikrotverdost' i Pribory" (Methods of Microhardness Testing and Apparatus) , 1965
174.
177
J. Henry
Proc. R. Irish Acad. , 1945
176.
Carbonsäuresynthesen mit 1, 1-Dichloräthylen
Bott K., Hellmann H.
Angewandte Chemie , 1966
179.
Über Adamantan und seine Derivate; Einige in 2-Stellung substituierte Derivate
Burkhard J., Vais J., Landa S.
Zeitschrift für Chemie , 2010
180.
183
Chem. Abs. , 1947
181.
184
F. Haurowitz
"The Chemistry and Function of Proteins" , 1965
182.
185
1954
183.
186
Chem. Abs. , 1956
184.
187
1954
185.
188
Chem. Abs. , 1955
186.
189
M. Godchot
Bull. Soc. chim. France (5) , 1913
187.
190
H. Law
J. Chem. Soc. , 1912
188.
191
M. Matsui
Mem. Coll. Sci., Kyoto Univ. , 1920
189.
192
E. Pannain
Rend. Classe Sci. fis. mat. nat. (5) , 1908
190.
193
E. Pannain
Gazzetta , 1909
191.
194
A. A. Vertman
"Svoistva Rasplavov Zheleza" (Properties of Iron Melts) , 1969
192.
195
M. Allen
J. Chem. Soc. , 1961
193.
196
E. Müller
Z. Elektrochem. , 1910
194.
197
J. Sicher
Chem. Listy , 1955
195.
198
W. Cohen
Rec. Trav. chim. , 1919
196.
199
Yu. K. Delimarskii
Byull. Izobr. , 1970
197.
200
Ref. Zh. Khim. , 1975
198.
201
A. Aladjem
1969
199.
202
G. Shiroa
Mem. Coll. Sci., Kyoto Univ. , 1930
200.
203
L. Andrieux
Compt. rend. , 1929
201.
204
Cherkesov A I
Ref. Zh. Khim. , 1968
202.
205
N. Bunge
Zhur. Russ. Fiz.-Khim. Obshch. , 1889
203.
206
J. Petersen
Z. Phys. Chem. , 1900
205.
208
O. A. Reutov
"Teoreticheskie Problemy Organicheskoi Khimii" (Theoretical Problems in Organic Chemistry) , 1956
206.
209
C. J. Haggerty
Trans. Am. Electrochem. Soc. , 1929
207.
210
H. L. Wheeler
Chem. Zentr. , 1908
208.
211
C. Schall
Z. Elektrochem. , 1923
210.
213
F. Yu. Rachinskii
"Khimiya Seraorganicheskikh Soedinenii, Soderzhashchikh-sya v Neftyakh i Nefteproduktakh" (Chemistry of Organo-sulphur Compounds Present in Petroleum and Petroleum Products) , 1966
212.
Synthesis of Adamantane Derivatives. I. Application of the Ritter Reaction to 1-Bromoadamantane
Sasaki T., Eguchi S., Toru T.
Bulletin of the Chemical Society of Japan , 1968
214.
217
1925
215.
218
Chem. Zentr. II , 1925
216.
219
G. I. Pustoshkin
Collected Papers "Biologicheskie Aktivnie Soedinenii" (Biologically Active Compounds) , 1955
217.
220
K. Ziegler
Angew. Chem. , 1955
218.
221
1960
219.
222
Chem. Abs. , 1961
221.
224
Chem. Abs. , 1959
222.
225
1960
225.
228
B. Roetheke
Chem. Abs. , 1959
226.
229
1959
227.
230
Chem. Abs. , 1962
228.
231
1960
229.
232
Chem. Abs. , 1960
230.
233
P. Cotter
J. Am. Chem. Soc. , 1956
231.
234
Ebach E A
Chem. Abs. , 1966
232.
235
R. Peffen
1967
233.
236
P. Peshev
Rev. internat. hautes Temperat. et Réfract. , 1969
234.
237
P. Peshev
Rev. internat. hautes Temperat. et Réfract. , 1969
235.
238
Brown G P
Am. Chem. Soc., Polymer Preprints , 1964
236.
239
Mendelbaum H. G.
Bull. Soc. chim. France , 1973
237.
240
W. A. Waters
"The Chemistry of Free Radicals" , 1948
238.
241
M. S. Kharasch
"Grignard Reactions of Nonmetallic Substances" , 1954
239.
242
N. N. Seroenov
"O Nekotorykh Problemakh Khimicheskoi Kinetiki i Reaktsionnoi Sposobnosti" (Some Problems in Chemical Kinetics and Reactivity) , 1958
240.
243
G. A. Kudintseva
1958
241.
244
C. Wilson
Record. Chem. Prog. , 1949
242.
245
G. A. Meerson
1958
243.
246
G. A. Meerson
Byull. Izobr. , 1968
244.
247
E. I. Levkoeva
Khim. Geterotsikl. Soed. , 1976
245.
248
M. Ya. Fioshin
Plasticheskie Massy , 1960
246.
249
A. I. Fedorova
Dokl. Akad. Nauk SSSR , 1961
247.
250
D. Goerrig
1955
248.
251
D. Goerrig
Chem. Abs. , 1959
249.
252
D. Goerrig
1956
250.
253
D. Goerrig
Chem. Abs. , 1959
251.
254
M. G. Safarov
1975
252.
255
Tomita M
Chem. Abs. , 1939
253.
256
Z. V. Zvonkova
Zh. Strukt. Khim. , 1977
254.
257
L. Ya. Markovskii
Zh. Neorg. Khim. , 1957
255.
258
P. P. Alexander
Metals Alloys , 1938
256.
259
V. Elyutin
Trudy Moskov. Inst. Stali , 1939
257.
260
C. Friedel
Compt. rend. , 1876