Home / Articles / Some new aspects in the application of perfluoroalkyl halides in the synthesis of fluorine-containing organic compounds

Some new aspects in the application of perfluoroalkyl halides in the synthesis of fluorine-containing organic compounds

Georgii Georgievich Furin 1
Georgii Georgievich Furin
1 N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistryof the Siberian Branch of Russian Academy of Sciences
10.1070/RC2000v069n06ABEH000353
Published 30 November 1999
Communication , Volume 69, Issue 6, 491-522
43
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Furin G. G. Some new aspects in the application of perfluoroalkyl halides in the synthesis of fluorine-containing organic compounds // Russian Chemical Reviews. 2000. Vol. 69. No. 6. pp. 491-522.
GOST all authors (up to 50)
Copy cite
Furin G. G. Some new aspects in the application of perfluoroalkyl halides in the synthesis of fluorine-containing organic compounds // Russian Chemical Reviews. 2000. Vol. 69. No. 6. pp. 491-522.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RC2000v069n06ABEH000353
UR - https://rcr.colab.ws/publications/10.1070/RC2000v069n06ABEH000353
TI - Some new aspects in the application of perfluoroalkyl halides in the synthesis of fluorine-containing organic compounds
T2 - Russian Chemical Reviews
AU - Furin, Georgii Georgievich
PY - 2000
DA - 1999/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 491-522
IS - 6
VL - 69
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{2000_Furin,
author = {Georgii Georgievich Furin},
title = {Some new aspects in the application of perfluoroalkyl halides in the synthesis of fluorine-containing organic compounds},
journal = {Russian Chemical Reviews},
year = {2000},
volume = {69},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC2000v069n06ABEH000353},
number = {6},
pages = {491--522},
doi = {10.1070/RC2000v069n06ABEH000353}
}
MLA
Cite this
MLA
Copy cite
Furin, Georgii Georgievich. “Some new aspects in the application of perfluoroalkyl halides in the synthesis of fluorine-containing organic compounds.” Russian Chemical Reviews, vol. 69, no. 6, Nov. 2000, pp. 491-522. https://rcr.colab.ws/publications/10.1070/RC2000v069n06ABEH000353.
Views / Visits / Downloads
13 / 13 / 2

Abstract

The approaches to the activation of perfluoroalkyl halides used as intermediates in the synthesis of partially fluorinated compounds are considered. The conditions for reactions of organic compounds with perfluoroalkyl iodides in the presence of reductants (Na2S2O4, HOCH2SO2Na), metals and metal salts, redox systems (Na2S2O8, ButOOH, Pb(OAc)4, H2O2–FeSO4, Ce(SO4)2) and transition metal complexes are described. The generation of perfluoroalkyl radicals by a single-electron transfer mechanism are discussed. The introduction of perfluoroalkyl groups into aromatic and unsaturated organic compounds and functionalisation of perfluoroalkyl iodides, particularly, their transformation into perfluoroalkanesulfinic and perfluoroalkanecarboxylic acids and aldehydes, are considered. The bibliography includes 442 references.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. , 1956
3.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) , 1952
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
11.
11
T. T. Bannister
Diss. Abstr. , 1959
15.
Preparation of esters containing an β-CF3 group
T. Purrington S., Stephen Everett T., Bumgardner C.L.
Tetrahedron Letters , 1984
16.
On the appearance of antiferroelectricity: The effect of polarization and conjugation in antiferroelectric liquid crystals
Suzuki Y., Nonaka O., Koide Y., Okabe N., Hagiwara T., Kawamura I., Yamamoto N., Yamada Y., Kitazume T.
Ferroelectrics , 1993
17.
Trifluoromethylated pyranose derivatives as the chiral dopant for ferroelectric liquid crystals
Itoh K., Takeda M., Namekawa M., Nayuki S., Murayama Y., Yamazaki T., Kitazume T.
Ferroelectrics , 1993
18.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
19.
Ferroelectric Liquid Crystal Mixtures Containing Chiral Pyranose Compounds for Response-Voltage Minimum Mode
Koden M., Kaneko T., Tamai K., Takeda H., Miyoshi S., Wada T., Takeda M., Itoh K., Yamazaki T., Kitazume T.
Japanese Journal of Applied Physics, Part 1: Regular Papers & Short Notes , 1994
20.
20
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
21.
Building blocks for the preparation of monofluoro organic compounds.
TAKEUCHI Y.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry , 1988
22.
Synthesis of trifluoromethyl azoles using building blocks.
TANAKA K., MITSUHASHI K.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry , 1987
25.
25
G. W. Robinson
J. Chem. Phys. , 1955
26.
26
B. Ya. Dain
1957
27.
27
A. A. Krasnovskii
Biofizika , 1956
28.
Reactions of electrophiles with polyfluorinated olefins
Petrov V.A., Bardin V.V.
Topics in Current Chemistry , 1997
30.
The Sulfinatodehalogenation Reaction
Huang W., Wu F.
Israel Journal of Chemistry , 1999
31.
31
A. A. Krasnovskii
Biokhimiya , 1960
32.
32
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
37.
37
L. M. Kosobutskaya
Dokl. Akad. Nauk SSSR , 1950
39.
Free-radical addition to olefins. Part 26.—Kinetics of the addition of trifluoromethyl radicals to acetylene and substituted acetylenes
El Soueni A., Tedder J.M., Walton J.C.
Journal of the Chemical Society Faraday Transactions 1 Physical Chemistry in Condensed Phases , 1981
41.
Photochemical perfluoroalkylation of imidazoles
Kimoto H., Fujii S., Cohen L.A.
Journal of Organic Chemistry , 1982
42.
Photochemical trifluoromethylation of some biologically significant imidazoles
Kimoto H., Fujii S., Cohen L.A.
Journal of Organic Chemistry , 1984
43.
Photochemical Trifluoromethylation of Some Aromatic and Heteroaromatic Compounds with Trifluoromethyl Bromide
Akiyama T., Kato K., Kajitani M., Sakaguchi Y., Nakamura J., Hayashi H., Sugimori A.
Bulletin of the Chemical Society of Japan , 1988
44.
Telomerization reactions in the synthesis of models for some fluorocarbon Polymers
Chambers R.D., Hutchinson J., Mobbs R.H., Musgrave W.K.
Tetrahedron , 1964
45.
An efficient electrochemical route to (perfluoroalkyl)alkynes
Calas P., Moreau P., Commeyras A.
Journal of the Chemical Society Chemical Communications , 1982
46.
Chemical reaction between the perfluoro-n-hexyl iodide and polarized mercury, yielding the perfluoro-n-hexyl mercuric iodide
Calas P., Moreau P., Commeyras A.
Journal of Electroanalytical Chemistry and Interfacial Electrochemistry , 1978
47.
Recent Advances in Trifluoromethylation.
UNEYAMA K.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry , 1991
50.
The Electronegativity of Groups
Huheey J.E.
The Journal of Physical Chemistry , 1965
51.
Fluoroalkylation of aromatic compounds
Cowell A.B., Tamborski C.
Journal of Fluorine Chemistry , 1981
52.
52
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
53.
53
D. Porretand E. Rabinowitch
Nature , 1937
54.
Convenient preparations and Michael reactions of 4-fluoroalkylated but-2-en-4-olides
Yoshida M., Imai R., Komatsu Y., Morinaga Y., Kamigata N., Iyoda M.
Journal of the Chemical Society Perkin Transactions 1 , 1993
55.
Direct heptafluoropropylation of purines with bis(heptafluorobutyryl) peroxide
Nishida M., Fujii S., Kimoto H., Hayakawa Y., Sawada H., Cohen L.A.
Journal of Fluorine Chemistry , 1993
56.
Trifluoromethylation of aromatic compounds with bis(trifluoroacetyl) peroxide
Sawada H., Nakayama M., Yoshida M., Yoshida T., Kamigata N.
Journal of Fluorine Chemistry , 1990
58.
Perfluoropropylation of Furans, Thiophenes, and Pyridines with Bis(heptafluorobutyryl) Peroxide
Sawada H., Yoshida M., Hagii H., Aoshima K., Kobayashi M.
Bulletin of the Chemical Society of Japan , 1986
59.
Perfluoroalkylations of nitrogen-containing heteroaromatic compounds with bis(perfluoroalkanoyl) peroxides
Yoshida M., Yoshida T., Kobayashi M., Kamigata N.
Journal of the Chemical Society Perkin Transactions 1 , 1989
60.
Heptafluoropropylation of Various Substituted Thiophenes with Bis(heptafluorobutyryl) Peroxide. Preparation of 3-Heptafluoropropylthiophene
Yoshida M., Yoshida T., Kamigata N., Kobayashi M.
Bulletin of the Chemical Society of Japan , 1988
61.
Perfluoropropylation of aromatic compounds with bis(heptafluorobutyryl) peroxide
Yoshida M., Amemiya H., Kobayashi M., Sawada H., Hagii H., Aoshima K.
Journal of the Chemical Society Chemical Communications , 1985
62.
62
A. A. Krasnovskii
"Sbornik, Voprosy Khimicheskoi Kinetiki" (Symposium, Problems of Chemical Kinetics) , 1955
63.
Synthesis of aromatic compounds containing perfluoro-oxa-alkyl groups
Sawada H., Nakayama M.
Journal of Fluorine Chemistry , 1991
64.
Synthesis, Fluorescence, and Photostabilities of 3‐(Perfluoroalkyl)coumarins
Matsui M., Shibata K., Muramatsu H., Sawada H., Nakayama M.
Chemische Berichte , 1992
65.
65
A. A. Krasnovskii
Biofizika , 1959
66.
Functionality of fluorine-containing dyes
Matsui M.
Journal of Fluorine Chemistry , 1999
68.
Generation and Synthetic Utilization of Highly Reactive Fluorinated Intermediates.
UNEYAMA K.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry , 1997
70.
Fluorinated free radicals
Dolbier W.R.
Topics in Current Chemistry , 1997
72.
Über die Darstellung von 5-Trifluormethyluracil
Hein L., Cech D.
Zeitschrift für Chemie , 2010
73.
Synthesis of fluorinated acetylenes
Baum K., Bedford C.D., Hunad R.J.
Journal of Organic Chemistry , 1982
74.
74
F. F. Litvin
Uspekhi Fiz. Nauk , 1960
75.
Addition thermique des iodo-1-perfluoroalcanes sur les perfluoroalkylethylenes
Jeanneaux F., Le Blanc M., Cambon A., Guion J.
Journal of Fluorine Chemistry , 1974
76.
76
A. N. Terenin
"Fotokhimiya Krasitelei" (The Photochemistry of Dyes) , 1947
80.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1937
83.
Cyclization Reactions of Perfluoroalkyl-Substituted Radicals
Brace N.O.
Journal of Organic Chemistry , 1966
84.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
88.
Effect of reaction conditions on the radical addition of perfluorohexyl iodide to vinyl acetate
Napoli M., Fraccaro C., Conte L., Gambaretto G.P., Legnaro E.
Journal of Fluorine Chemistry , 1992
89.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow , 1955
90.
90
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1951
91.
Condensation of perfluoroalkyl iodides with unsaturated nitrogen compounds
Cantacuzène D., Wakselman C., Dorme R.
Journal of the Chemical Society Perkin Transactions 1 , 1977
92.
Recent trends in research into ionic polymerisation
Erusalimskii B.L.
Russian Chemical Reviews , 1992
93.
Iodoperfluoroalkanes
Deev L.E., Nazarenko T.I., Pashkevich K.I., Ponomarev V.G.
Russian Chemical Reviews , 1992
95.
95
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
96.
96
L. M. Vorob'eva
Biokhimiya , 1958
97.
97
A. N. Terenin
Dokl. Akad. Nauk SSSR , 1952
98.
98
W. Franke
Chem. Zentr. , 1954
99.
99
V. V. Zolotarev
1938
100.
Phase-transfer catalysed ion-radical perfluoroalkylation of thiols
Popov V.I., Boiko V.N., Yagupolskii L.M.
Journal of Fluorine Chemistry , 1982
101.
101
M. F. Shostakovskii
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
102.
102
F. Fichter
Helv. Chim. Acta , 1922
103.
Perfluoroalkylation of thiols by pefluoroalkylbromides
Ignatev N.V., Boiko V.N., Yagupolskii L.M.
Journal of Fluorine Chemistry , 1985
104.
104
O. P. Osipova
Dokl. Akad. Nauk SSSR , 1950
105.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR , 1958
106.
106
F. Fichter
Helv. Chim. Acta , 1927
107.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. , 1961
110.
A new convenient method for the synthesis of perfluoroalkylarylsulfides
Koshechko V.G., Kiprianova L.A., Fileleeva L.I.
Tetrahedron Letters , 1992
113.
Electrochemical initiation by sulfur dioxide of radical-chain trifluoromethylation processes of thiophenols with bromotrifluoromethane
Koshechko V.G., Kiprianova L.A., Fileleeva L.I., Rozhkova Z.Z.
Journal of Fluorine Chemistry , 1995
115.
Synthesis of (perfluoroalkylsulfonyl)benzenes
Joglekar B., Miyake T., Kawase R., Shibata K., Muramatsu H., Matsui M.
Journal of Fluorine Chemistry , 1995
116.
Dvořák D., Neugebauerová E., Liška F., Ludvík J.
Collection of Czechoslovak Chemical Communications , 2002
117.
Studies on fluoroalkylation and fluoroalkoxylation. Regioselective synthesis of fluoroalkylated imidazoles
Chen Q., Qiu Z.
Journal of the Chemical Society Chemical Communications , 1987
118.
118
V. M. Rodionov
Zhur. Obshch. Khim. , 1935
119.
119
V. V. Levchenko
Zhur. Obshch. Khim. , 1947
121.
121
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
123.
123
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
126.
Perfluoroalkyl-selenation of olefins
Uneyama K., Kitagawa K., Kitagawa K.
Tetrahedron Letters , 1991
127.
127
R. Pasternak
Helv. Chim. Acta , 1948
128.
128
J. Wiemann
Bull. Soc. chim. France , 1952
129.
Reactions of bromotrifluoromethane and related halides: synthesis of trifluoromethyl sulphides from disulphides
Wakselman C., Tordeux M., Clavel J., Langlois B.
Journal of the Chemical Society Chemical Communications , 1991
131.
Characterization of novel TCNQ and TCNE 1:1 and 1:2 salts of the tetrakis(dimethyamino)ethylene dication, [{(CH3)2N}2C–C{N(CH3)2}2]2+
Fox J.R., Foxman B.M., Guarrera D., Miller J.S., Calabrese J.C., Reis A.H.
Journal of Materials Chemistry A , 1996
136.
136
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1954
137.
Reaction of perfluoroalkylhalogenides with olefins in the presence of alcoholic alkali
Igumnov S.M., Pletnev C.I., Bil'dinov I.K., Podsevanov P.V., Sayanov A.A., Alexeev A.N., Bobrinev S.V.
Journal of Fluorine Chemistry , 1992
138.
138
S. Ono
J. Chem. Soc. Japan , 1957
139.
The Iowa connection
Burton D.J.
Journal of Fluorine Chemistry , 1999
141.
141
Friedl.
142.
142
1913
143.
143
Friedl.
144.
144
1912
145.
145
Friedl.
146.
146
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1952
148.
148
P. Kresse
Chem. Abs. , 1960
150.
150
Ya. E. Bernadskaya
"Iskusstvennoe Volokno" (Artificial Fibres) , 1952
151.
151
V. M. Rodionov
Zhur. Obshch. Khim. , 1936
152.
152
W. Albert
Trans. Electrochem. Soc. , 1943
153.
A Novel Nucleophilic Polyfluoroalkylating Agent RfIP(NEt2)3
Huang W., Hu C., He Y., Zhou H.
Journal of Fluorine Chemistry , 1990
154.
154
Friedl.
155.
155
M. V. Mal'tsev
Izv. Vys. Ucheb. Zaved., Tsvet. Met. , 1960
156.
156
J. S. Fruton
J. Biol. Med. , 1950
157.
157
1903
158.
158
Friedl.
159.
159
J. Tafel
Z. Elektrochem. , 1911
160.
160
1912
163.
163
Friedl.
166.
Fragmentation of aryl sulfide radical anions during aromatic SRN1 reactions
Bunnett J.F., Creary X.
Journal of Organic Chemistry , 1975
168.
Aromatic substitution by the SRN1 mechanism
Bunnett J.F.
Accounts of Chemical Research , 1978
169.
169
Friedl.
170.
170
1918
171.
171
Friedl.
172.
172
1918
174.
174
S. Calvert
India Rubber Tire Rev. , 1926
175.
175
I. Mayer
1966
176.
176
G. V. Samsonov
"Metody Ispytaniya na Mikrotverdost' i Pribory" (Methods of Microhardness Testing and Apparatus) , 1965
177.
177
J. Henry
Proc. R. Irish Acad. , 1945
178.
178
1946
179.
Rossi R.A., Pierini A.B., Peñéñory A.B.
1995
180.
180
1946
181.
181
Chem. Abs. , 1947
182.
182
1947
183.
183
Chem. Abs. , 1947
184.
184
F. Haurowitz
"The Chemistry and Function of Proteins" , 1965
185.
185
1954
186.
186
Chem. Abs. , 1956
187.
187
1954
188.
Reactions of tertiary perfluoroalkyl halides with halide anions
Blume E., Gasafi-Martin W., Probst A., von Werner K.
Journal of Fluorine Chemistry , 1991
189.
189
M. Godchot
Bull. Soc. chim. France (5) , 1913
190.
190
H. Law
J. Chem. Soc. , 1912
191.
191
M. Matsui
Mem. Coll. Sci., Kyoto Univ. , 1920
192.
192
E. Pannain
Rend. Classe Sci. fis. mat. nat. (5) , 1908
193.
193
E. Pannain
Gazzetta , 1909
196.
196
E. Müller
Z. Elektrochem. , 1910
197.
197
J. Sicher
Chem. Listy , 1955
198.
Preparation of ?,?-difluoromethylene functionalized sulfones
Yang Z., Burton D.J.
Heteroatom Chemistry , 1992
202.
Palladium-catalysed alkynyl-dehydroxylation of polyfluorophenols
Chen Q., Li Z.
Journal of the Chemical Society Perkin Transactions 1 , 1992
204.
204
Cherkesov A I
Ref. Zh. Khim. , 1968
205.
205
N. Bunge
Zhur. Russ. Fiz.-Khim. Obshch. , 1889
206.
206
J. Petersen
Z. Phys. Chem. , 1900
207.
207
F. Fichter
"Organische Elektrochemie" , 1942
208.
208
O. A. Reutov
"Teoreticheskie Problemy Organicheskoi Khimii" (Theoretical Problems in Organic Chemistry) , 1956
209.
209
C. J. Haggerty
Trans. Am. Electrochem. Soc. , 1929
210.
210
H. L. Wheeler
Chem. Zentr. , 1908
211.
PREPARATION OF 2-SUBSTITUTED ETHYL PERFLUOROALKYLSULFONES
Zhu S.Z., Qin C.Y., Xu B.
Phosphorus, Sulfur and Silicon and the Related Elements , 1996
212.
212
L. V. Pavlova
Zh. Obshch. Khim. , 1965
213.
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
214.
214
L. V. Pavlova
1965
216.
216
A. P. Tomilov
Zhur. Prikl. Khim. , 1959
217.
Twisted polyaza clefts for the complexation of cyclohexane-polyols
Huang C., Cabell L.A., Anslyn E.V.
Tetrahedron Letters , 1990
219.
219
G. I. Pustoshkin
Collected Papers "Biologicheskie Aktivnie Soedinenii" (Biologically Active Compounds) , 1955
220.
220
K. Ziegler
Angew. Chem. , 1955
221.
221
1960
222.
222
Chem. Abs. , 1961
223.
223
1959
224.
224
Chem. Abs. , 1959
226.
226
Chem. Abs. , 1961
227.
227
B. Roetheke
1958
232.
A new method for the preparation of perfluorocarboxylic acids
Huang B., Haas A., Lieb M.
Journal of Fluorine Chemistry , 1987
235.
Perfluoroalkylation of anilines in the presence of zinc and sulphur dioxide
Wakselman C., Tordeux M.
Journal of the Chemical Society Chemical Communications , 1987
236.
236
P. Peshev
Rev. internat. hautes Temperat. et Réfract. , 1969
237.
237
P. Peshev
Rev. internat. hautes Temperat. et Réfract. , 1969
239.
239
Mendelbaum H. G.
Bull. Soc. chim. France , 1973
240.
240
W. A. Waters
"The Chemistry of Free Radicals" , 1948
241.
241
M. S. Kharasch
"Grignard Reactions of Nonmetallic Substances" , 1954
242.
242
N. N. Seroenov
"O Nekotorykh Problemakh Khimicheskoi Kinetiki i Reaktsionnoi Sposobnosti" (Some Problems in Chemical Kinetics and Reactivity) , 1958
244.
244
C. Wilson
Record. Chem. Prog. , 1949
245.
245
G. A. Meerson
1958
246.
246
G. A. Meerson
Byull. Izobr. , 1968
247.
247
E. I. Levkoeva
Khim. Geterotsikl. Soed. , 1976
248.
248
M. Ya. Fioshin
Plasticheskie Massy , 1960
249.
249
A. I. Fedorova
Dokl. Akad. Nauk SSSR , 1961
251.
A new approach to polyfluoroalkyl imidoyl iodide
Yu H., Huang W.
Tetrahedron Letters , 1996
252.
252
D. Goerrig
1956
253.
253
D. Goerrig
Chem. Abs. , 1959
256.
256
Z. V. Zvonkova
Zh. Strukt. Khim. , 1977
258.
258
P. P. Alexander
Metals Alloys , 1938
260.
260
C. Friedel
Compt. rend. , 1876
261.
Synthesis of cholesterol and its analogs with fluorinated side-chains
Huang W., Hu L., Ge W.
Journal of Fluorine Chemistry , 1989
263.
263
R. E. Spivak
Azerb. Neft. Khoz. , 1975
264.
Direct synthesis of 3-(fluoroalkyl)pyrazoles from polyfluoroalkyl aldehydes
Tang X., Hu C.
Journal of the Chemical Society Perkin Transactions 1 , 1994
265.
265
E. A. Ostroumov
Zavod. Lab. , 1935
266.
266
N. G. Mudrik
1975
267.
267
V. A. Epel'baum
Zh. Fiz. Khim. , 1940
268.
268
L. N. Shkaraputa
1975
269.
269
Sharma V N
J. Indian Chem. Soc. , 1935
270.
270
N. Whitehouse
J. Soc. Chem. Ind. , 1907
271.
271
Stepanov B I
Zh. Obshch. Khim. , 1962
272.
272
J. Johnston
Edin. J. Sci. (New Ser.) , 1831
273.
273
J. Johnston
Edin. J. Sci. (New Ser.) , 1831
274.
274
J. Johnston
Edin. J. Sci. (New Ser.) , 1831
275.
Radical reactions in natural product synthesis
Jasperse C.P., Curran D.P., Fevig T.L.
Chemical Reviews , 1991
276.
276
St. C. H. Deville
Ann. Chim. Phys. , 1859
277.
277
St. C. H. Deville
Ann. Chim. Phys. , 1859
278.
278
L. Troost
Compt. rend. , 1865
280.
280
B. de Jassonneix
Compt. rend. , 1906
281.
A Convenient Synthesis of Perfluoroalkylated and Fluorinated-Aryl Nitrogen Bases by Electrochemically Induced SRN1 Substitution
Médebielle M., Oturan M.A., Pinson J., Savéant J.
Journal of Organic Chemistry , 1996
282.
Synthesis of 5-per(poly)fluoroalkyl-2,3-dihydro-1,4-diazepines
Wang Q., Hu B., Luo B., Hu C.
Tetrahedron Letters , 1998
283.
283
H. Moissan
Compt. rend. , 1902
284.
284
H. Moissan
Compt. rend. , 1902
285.
One-pot reaction for the synthesis of fluorinated β-diketones
Huang W., Wu Y.
Journal of Fluorine Chemistry , 1992
286.
286
W. Schedler
1902
288.
288
Bogdanov G N
1981
290.
290
Guntz
Compt. rend. , 1902
292.
292
Pechernikova Z P
Zavod. Lab. , 1978
294.
294
H. I. Schlesinger
J. Am. Chem. Soc. , 1937
295.
295
Burlakova E B
Dokl. Akad. Nauk SSSR , 1965
296.
296
H. I. Schlesinger
J. Am. Chem. Soc. , 1940
298.
298
J. F. Hardy
1968
300.
300
P. P. Alexander
Chem. Abs. , 1949
301.
301
N. Razkazov
"Metalokeramika Spets. Splavi i Kontaktni Materiali" (Powder Metallurgy, Special Alloys, and Contact Materials) , 1967
302.
302
N. Razkazov
1969
305.
305
T. Yano
1968
306.
A novel synthesis of α-(perfluoroalkyl) ketones
Hu C., Tang X., Qing F.
Journal of Fluorine Chemistry , 1992
308.
308
R. G. Shumilova
Poroshk. Met. , 1968
310.
The reaction of sodium perfluoroalkanesufinates with coumarin
Liu J., Huang W.
Journal of Fluorine Chemistry , 1999
311.
Highly fluorinated systems for oxygen transport, diagnosis and drug delivery
Riess J.G.
Colloids and Surfaces A: Physicochemical and Engineering Aspects , 1994
313.
313
Gavrilov V. I.
Elektrokhimiya , 1980
315.
315
S. Imai
1967
316.
Synthesis of perfluoroalkyl-containing steroidal glycosides
Huang W., Lü L.
Chinese Journal of Chemistry , 2010
317.
317
P. A. Smudski
1968
318.
318
1968
319.
319
S. M. H. Ito
1970
322.
Perfluoroalkylation of aromatics
Huang W., Ying W., Zhang H., Liu J.
Chinese Journal of Chemistry , 2010
323.
323
S. Ozaki
Rep. Govt. Ind. Res. Inst. Nagoua , 1968
324.
324
H. A. Ohlgren
1969
325.
325
G. A. Meerson
Neorg. Materialy , 1970
326.
326
1969
327.
327
E. J. Goon
1967
328.
328
J. D. Flexonand H. N. Troy
1968
329.
329
J. Petlicka
Hutnik , 1970
330.
330
G. D. Mazaletskii
1970
331.
331
G. D. Mazaletskii
1969
333.
333
G. A. Sorokin
1970
334.
334
L. E. Gorbunov
Poroshk. Met. , 1966
335.
335
A. C. Byrns
1967
336.
Reactions of olefinic double bonds with polyfluoroalkyl radicals generated electrochemically
Brookes C.J., Coe P.L., Owen D.M., Pedler A.E., Tatlow J.C.
Journal of the Chemical Society Chemical Communications , 1974
337.
337
B. Matchen
1968
338.
Reactions of fluoroalkyl radicals generated electrochemically. Part 1. Additions of trifluoromethyl radicals to olefinic and acetylenic bonds
Brookes C.J., Coe P.L., Pedler A.E., Tatlow J.C.
Journal of the Chemical Society Perkin Transactions 1 , 1978
340.
340
E. Clar
1967
342.
342
Z. Crha
1970
343.
343
K. Langrod
1969
344.
344
H. Lott
1969
347.
347
J. Dziadur
1968
348.
Iron-catalyzed addition reaction of fluoroalkyl iodides to alkenes
Chen Q., He Y., Yang Z.
Journal of Fluorine Chemistry , 1986
349.
Novel and practical preparation of α-fluoro-functionalized esters from fluoroiodoacetates
Zhi C., Chen Q.
Journal of the Chemical Society Perkin Transactions 1 , 1996
351.
351
M. Ya. Popil'skii
1969
352.
352
M. Ya. Popil'skii
Byull. Izobr. , 1970
354.
354
G. N. Bogachov
1970
355.
355
G. N. Bogachov
Byull. Izobr. , 1970
356.
356
B. G. Pozharskii
1969
358.
Copper chloride-ethanolamine catalyzed addition of polyhaloalkanes to 1-octene
Burton D.J., Kehoe L.J.
Journal of Organic Chemistry , 1970
359.
A new addition of fluoroalkyl iodides to alkenes catalysed by raney nickel
Chen Q., Yang Z.
Journal of the Chemical Society Chemical Communications , 1986
360.
360
J. Wlodyka
Rudy i Metale niezel. , 1970
361.
361
J. Wlodyka
1971
363.
363
S. African Mining Eng. J. , 1969
364.
364
S. African Mining Eng. J. , 1969
365.
365
S. African Mining Eng. J. , 1969
366.
366
S. African Mining Eng. J. , 1969
367.
367
G. A. Meerson
Neorg. Materialy , 1969
368.
368
A. E. van Arkel
Chem. Weekblad , 1927
369.
Reaction of trifluoromethanesulphonyl chloride with alkenes catalysed by a ruthenium(II) complex
Kamigata N., Fukushima T., Yoshida M.
Journal of the Chemical Society Chemical Communications , 1989
371.
Triethylborane-induced stereoselective radical addition of perfluoroalkyl iodides to acetylenes
Takeyama Y., Ichinose Y., Oshima K., Utimoto K.
Tetrahedron Letters , 1989
372.
372
A. E. van Arkel
Physica , 1924
373.
373
A. E. van Arkel
Physica , 1924
375.
Triethylborane Induced Perfluoroalkylation of Silyl Enol Ethers and Ketene Silyl Acetals with Perfluoroalkyl Iodides
Miura K., Takeyama Y., Oshima K., Utimoto K.
Bulletin of the Chemical Society of Japan , 1991
376.
Diastereoselective introduction of an EtO2CCF2-group into chiral imide enolates mediated by triethylborane
Iseki K., Asada D., Takahashi M., Nagai T., Kobayashi Y.
Tetrahedron Letters , 1994
377.
377
Karayama M.
Ref. Zh. Khim. , 1982
379.
379
O. Meyer-Simon
1968
380.
380
B. P. Sereda
1968
381.
381
B. P. Sereda
Byull. Izobr. , 1968
382.
382
A. N. Selikman
"Tugoplavkie Metally" (High-melting Metals) , 1968
383.
383
H. Walther
1943
384.
384
V. F. Funken
Poroshk. Met. , 1969
385.
385
J. Cueilleron
1967
387.
387
M. Kawakami
1968
388.
388
R. A. Paris
Chimie et Industrie , 1968
389.
389
M. Kawakami
1967
390.
390
M. Kawakami
1968
391.
Solvents effects in reactions between perfluoroalkyliodides and cadmium
Chen G.J., Tamborski C.
Journal of Fluorine Chemistry , 1987
394.
Perfluoroalkylbenzenesulfonyl chlorides, perfluoroalkylnaphthalenesulfonyl chlorides, and their metal salts
Paciorek K.J., Kratzer R.H., Nakahara J.H., Atkins H.M.
Journal of Fluorine Chemistry , 1991
395.
Perfluoroalkylcopper(I) compounds
L. Coe P., E. Milner N.
Journal of Organometallic Chemistry , 1972
400.
A novel synthesis of per(poly)fluoroalkyl aldehydes
Hu C., Tang X.
Journal of Fluorine Chemistry , 1993
404.
404
K. W. Richardson
1968
407.
Ultrasound-promoted selective perfluoroalkylation on the desired position of organic molecules
Kitazume T., Ishikawa N.
Journal of the American Chemical Society , 1985
408.
Synthèse d'acides ω perfluoroalkylalcanoı̈ques et d'ω perfluoroalkylalcanols
Tra Anh D., Blancou H., Commeyras A.
Journal of Fluorine Chemistry , 1999
409.
409
C. B. Wendel
1967
410.
410
D. Cleaver
1967
411.
411
H. Brünner
1968
412.
ASYMMETRIC ADDITION OF PERFLUOROALKYL GROUPS ON CARBONYLS WITH ZINC AND ULTRASOUND
Solladie-Cavallo A., Farkhani D., Fritz S., Lazrak T., Suffert J.
Tetrahedron Letters , 1984
413.
413
E. Curtis
1968
414.
414
M. P. Freeman
1969
415.
Studies on the reaction of cupric(II) perfluoroalkanesulfinate
Huang W., Xie Y.
Chinese Journal of Chemistry , 1990
416.
416
E. K. Safronov
Byull. Izobr. , 1970
418.
418
G. Bliznakov
Bull. Acad. bulg. Sci., Sect. Sci. chim. , 1969
419.
419
W. R. Wilcox
Trans. Metall. Soc. AIME , 1968
422.
422
423.
423
W. Kleber
Monatsber. , 1969
424.
Synthesis of functionalized compounds containing a difluoromethylene moiety
Chen J., Hu C.
Journal of the Chemical Society Perkin Transactions 1 , 1994
425.
Alkoxyperfluoroalkylation of enol ethers catalysed by iron complexes
Sasaoka S., Uno M., Joh T., Lmazaki H., Takahashi S.
Journal of the Chemical Society Chemical Communications , 1991
427.
427
N. R. McGabe
1969
428.
428
P. M. Jones
1969
429.
429
1969
430.
430
V. D. Aftandilian
1969
432.
432
W. L. Wilson
1969
433.
433
E. S. Monroe
1969
434.
434
D. Raicevic
1969
435.
435
E. J. Curtis
1969
436.
436
W. L. Wilson
1969
437.
437
W. L. Wilson
1969
438.
438
1969
439.
Synthesis of polyfluorinated aromatic polyesters
Zhang L., Huang W.
Journal of Fluorine Chemistry , 2000
440.
440
Yu. M. Dmitrievand N. V. Galitskii
Byull. Izobr. , 1970
441.
441
T. S. te Velde
Philips techn. Tijdschr. , 1969
442.
442
K. E. Spear
High-temp. Sci. , 1969
445.
445
H. A. Johansen
Planseeber. Pulvermetallurgie , 1970
446.
446
Kh. Erinin
Trudy Fil. NIPKIEP, Metalokeramika, Spetssplavi i Kontaktni Materiali , 1968
447.
447
Kh. Erinin
Trudy Fil. NIPKIEP, Metalokeramika, Spetssplavi i Kontaktni Materiali , 1968
448.
448
Kh. Erinin
1970
449.
449
M. Déchamps
Compt. rend. , 1970
450.
450
V. N. Svechnikov
Dokl. Akad. Nauk SSSR, Ser. Khim. , 1970
452.
452
V. N. Gurin
Neorg. Materialy , 1970
453.
453
V. B. Golyshev
1969
454.
454
V. B. Golyshev
Ref. Zh. Khim. , 1970
455.
Novel perfluoroalkylation of alkenes with perfluoroalkanesulphonyl chlorides catalysed by a ruthenium(II) complex
Kamigata N., Fukushima T., Terakawa Y., Yoshida M., Sawada H.
Journal of the Chemical Society Perkin Transactions 1 , 1991
456.
456
D. M. Hausen
1969
457.
Direct perfluoroalkylation of aromatic and heteroaromatic compounds with perfluoroalkanesulfonyl chlorides catalysed by a ruthenium(II) phosphine complex
Kamigata N., Ohtsuka T., Fukushima T., Yoshida M., Shimizu T.
Journal of the Chemical Society Perkin Transactions 1 , 1994
458.
458
V. B. Golyshev
Byull. Izobr. , 1970
459.
459
Chem. Abstr. , 1979
460.
Stereoselectivity in 4πs+4πs photocycloaddition of 1,3-cyclohexadiene to arenes
Yang N.C., Gan H., Sung S.K., Masnovi J.M., Rafalko P.W., Ezell E.F., Lenz G.R.
Tetrahedron Letters , 1990
461.
A convenient synthesis of fluoro-aromatic acetylene derivatives
Yadong Z., Jianxun W.
Journal of Fluorine Chemistry , 1990
463.
General method for the preparation of functionalized fluorinated phenyl alkynes
Nguyen B.V., Yang Z.Y., Burton D.J.
Journal of Organic Chemistry , 1993
464.
464
P. D. S. St. Pierre
1969
465.
465
O. Matsumoto
J. Electrochem. Soc. Japan , 1967
466.
466
M. P. Freeman
1966
467.
Palladium-catalyzed syntheses of conjugated polyenes
Heck R.F.
Pure and Applied Chemistry , 1981
469.
469
H. Triche
Methods Phys. Analysis , 1969
470.
470
471.
Cyclization reactivities of fluorinated hex-5-enyl radicals
Dolbier Jr., W.R., Rong X.X., Bartberger M.D., Koroniak H., Smart B.E., Yang Z.
Journal of the Chemical Society Perkin Transactions 2 , 1998
472.
472
H. Winterhager
Ber. deutsch. Ceram Ges. , 1969
473.
473
T. Kaze
1969
474.
474
T. Kaze
1970
475.
475
D. M. Chizhikov
1969
476.
476
D. M. Chizhikov
1970
477.
477
U. A. Tsielen
Izd. Latv. SSR, Ser. Khim. , 1970
478.
478
"Nizkotemperaturnaya Plazma v Tekhnologii Neorganicheskikh Veshchestv" (Low-temperature Plasma in Inorganic Technology) , 1971
482.
482
H. Sasaki
1968
483.
483
H. Sasaki
1969
484.
A facile synthesis of .alpha.,.omega.-dicarboxylic acids containing perfluoroalkylene groups
Urata H., Kinoshita Y., Asanuma T., Kosukegawa O., Fuchikami T.
Journal of Organic Chemistry , 1991
485.
Transformations of F-Alkyl Iodides and Bromides Induced by Nickel(0) Carbonyl
Krespan C.G., Dixon D.A.
Journal of Organic Chemistry , 1998
486.
F-alkyliron(II) compounds
Krespan C.G.
Journal of Fluorine Chemistry , 1988
488.
488
Grechkin N P
Izv. Akad. Nauk SSSR, Ser. Khim. , 1968
489.
489
Petrov K A
Zh. Obshch. Khim. , 1962
490.
490
491.
491
Romanenko V D
Zh. Obshch. Khim. , 1984
492.
492
Romanenko V D
Zh. Obshch. Khim. , 1987
493.
Selective allylic electron-transfer oxidation of β-ionone
Calo V., Lopez L., Troisi L.
Journal of the Chemical Society Chemical Communications , 1989
495.
495
Hudson R F
Structure and Mechanism in Organophosphorus Chemistry , 1984
496.
496
Hudson R F
Structure and Mechanism in Organophosphorus Chemistry , 1967
497.
497
Pudovik A N
Zh. Obshch. Khim. , 1975
498.
498
Gilyarov V A
Zh. Obshch. Khim. , 1966
500.
500
Peiffer G
C. R. Hebd. Seances Acad. Sci. , 1968
502.
502
Yu G Trishin
Zh. Org. Khim. , 1975
505.
Radical-cations as intermediates in the oxidation of alkenes by metal ions
Norman J.A., Thomas C.B., Burrow M.J.
Journal of the Chemical Society Perkin Transactions 1 , 1985
506.
506
508.
Electrochemical reactions of fluoro organic compounds
Fuchigami T.
Topics in Current Chemistry , 1994
511.
511
Gurevich P A
Zh. Obshch. Khim. , 1985
512.
Chemical Redox Agents for Organometallic Chemistry
Connelly N.G., Geiger W.E.
Chemical Reviews , 1996
513.
Mechanistic Criteria for Cation Radical Reactions: Aminium Salt-Catalyzed Cyclopropanation
Yueh W., Bauld N.L.
Journal of the American Chemical Society , 1995
514.
514
516.
Reactivity of the electrogenerated superoxide O2− anion with α, ω-diiodoperfluorobutane. Synthesis of 4-iodoperfluorobutanoic acid
Dapremont-Avignon C., Calas P., Amatore C., Bénéfice-Malouet S., Commeyras A.
Journal of Fluorine Chemistry , 1996
517.
Synthesis of perfluoroalkyl carboxylic acids by reaction of perfluoroalkyl iodides with electrogenerated superoxide ion
Dapremont-avignon C., Calas P., Commeyras A., Amatore C.
Journal of Fluorine Chemistry , 1991
518.
518
519.
519
Ref. Zh. Khim. , 1969
520.
520
Pudovik A N
Zh. Obshch. Khim. , 1971
522.
522
Predvoditelev D A
Zh. Obshch. Khim. , 1973
523.
523
Mizrakh L I
Zh. Obshch. Khim. , 1976
525.
Cation-radicals: formation of methoxy-radicals by photochemical and thermal oxidation of methanol
Ledwith A., Russell P.J., Sutcliffe L.H.
Journal of the Chemical Society D Chemical Communications , 1971
526.
ESR Studies of the Sulfite Radical Anion
Ozawa T., Setaka M., Kwan T.
Bulletin of the Chemical Society of Japan , 1971
527.
527
Pudovik M A
Zh. Obshch. Khim. , 1974
528.
528
530.
530
531.
531
Chem. Abstr. , 1985
532.
532
533.
533
Chem. Abstr. , 1982
534.
Synthesis of perfluoroalkylthioethers from disulfides
Torduex M., Wakselman C., Clavel J.L., Langlois B., Nantermet R.
Journal of Fluorine Chemistry , 1991
535.
Trifluoromethylation with sodium trifluoromethanesulfinate under oxidative conditions
Clavel J.L., Langlois B., Laurent E., Roidot N.
Journal of Fluorine Chemistry , 1991
537.
537
E E Nifant'ev
Zh. Obshch. Khim. , 1966
538.
538
Rumyantseva S A
Zh. Obshch. Khim. , 1984
539.
539
G Yu Gadzhiev
Zh. Obshch. Khim. , 1986
540.
540
E E Nifant'ev
Koord. Khim. , 1979
541.
541
Pavlov V A
Izv. Akad. Nauk SSSR, Ser. Khim. , 1980
543.
543
Sanchez M
Bull. Soc. Chim. Fr. , 1967
544.
544
Pudovik A N
Zh. Obshch. Khim. , 1971
546.
Radicals and scavengers. 7. Diffusion controlled scavenging of phenyl radicals and absolute rate constants of several phenyl radical reactions
Kryger R.G., Lorand J.P., Stevens N.R., Herron N.R.
Journal of the American Chemical Society , 1977
547.
547
Bernard D
C. R. Hebd. Seances Acad. Sci. , 1973
548.
Polar Effects in Free-Radical Reactions. The Paradox of Reduction of Alkyl Iodides and Reductive Alkylation of Alkenes by Strong Oxidants (t-BuOOH, Pb(OAc)4)
Minisci F., Fontana F., Recupero F., Bravo A., Pagano E., Rinaldi C., di Luca M., Grossi F., Bjørsvik H.
Journal of the American Chemical Society , 1999
549.
549