Home / Articles / N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis

N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis

Georgii Georgievich Furin 1
Georgii Georgievich Furin
, 
Al'bert Aleksandrovich Fainzil'berg 2
Al'bert Aleksandrovich Fainzil'berg
1 Novosibirsk Institute of Organic Chemistryof the Siberian Branch of Russian Academy of Sciences
2 N. D. Zelinskii Institute of Organic Chemistry, Moscow
10.1070/RC1999v068n08ABEH000293
Published 30 November 1998
Communication , Volume 68, Issue 8, 653-684
33
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Furin G. G., Fainzil'berg A. A. N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis // Russian Chemical Reviews. 1999. Vol. 68. No. 8. pp. 653-684.
GOST all authors (up to 50)
Copy cite
Furin G. G., Fainzil'berg A. A. N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis // Russian Chemical Reviews. 1999. Vol. 68. No. 8. pp. 653-684.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RC1999v068n08ABEH000293
UR - https://rcr.colab.ws/publications/10.1070/RC1999v068n08ABEH000293
TI - N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis
T2 - Russian Chemical Reviews
AU - Furin, Georgii Georgievich
AU - Fainzil'berg, Al'bert Aleksandrovich
PY - 1999
DA - 1998/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 653-684
IS - 8
VL - 68
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{1999_Furin,
author = {Georgii Georgievich Furin and Al'bert Aleksandrovich Fainzil'berg},
title = {N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis},
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/RC1999v068n08ABEH000293},
number = {8},
pages = {653--684},
doi = {10.1070/RC1999v068n08ABEH000293}
}
MLA
Cite this
MLA
Copy cite
Furin, Georgii Georgievich, and Al'bert Aleksandrovich Fainzil'berg. “N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis.” Russian Chemical Reviews, vol. 68, no. 8, Nov. 1999, pp. 653-684. https://rcr.colab.ws/publications/10.1070/RC1999v068n08ABEH000293.
Views / Visits / Downloads
21 / 21 / 3

Abstract

The data on the synthesis and application in organic synthesis of fluorinating compounds containing N–F bonds are surveyed and systematised. The reagents are classified into two categories, viz., neutral (perfluoro-N-fluoropiperidine, N-fluoro-2-pyridone, N-fluorosulfonamides, N-fluoro-N-alkylamides, N-fluorobis(trifluoromethyl)sulfonylamine, N-fluorobenzo-1,3,2-dithiazole 1,1,3,3-tetroxide, N-fluoro sultams) and ionic reagents (N-fluoropyridinium, N-fluoroquinuclidinium and 1-alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts). A comparative analysis of the fluorinating activity of the reagents depending on their structure and the nature of the solvent is carried out taking into account theoretical calculations. The possibility of fluorination of various classes of organic compounds is discussed. The mechanisms of fluorination with N–F compounds are analysed using kinetic data. The advantages and disadvantages of N-fluoro amines in comparison with elemental fluorine, xenon difluoride and other fluorinating reagents are considered. The influence of the nature of the solvent on the fluorinating activity of N-fluoro amines and their analogues is discussed. The bibliography includes 245 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.
Recent Development of Fluorinating Agents.
UMEMOTO T.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry , 1992
7.
Electrophilic NF Fluorinating Agents
Lal G.S., Pez G.P., Syvret R.G.
Chemical Reviews , 1996
9.
9
V. H. Lynch
Carnegie Inst. Year Book , 1954
10.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959
11.
11
T. T. Bannister
Diss. Abstr. , 1959
12.
12
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
13.
13
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
14.
14
V. B. Evstigneev
Zhur. Fiz. Khim. , 1958
15.
15
A. S. Holt
"Research in Photosynthesis" , 1957
16.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
17.
N-Fluoropyridinium Salts
Strekowski L., Kiselyov A.S.
Advances in Heterocyclic Chemistry , 1995
19.
19
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1959
20.
20
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
21.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
22.
22
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
23.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR , 1958
24.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR , 1951
25.
Redox properties of electrophilic fluorination reagents of the N-F class
Pez G.P., Gilicinski A.G., Syvret R.G., Sankar Lal G.
Journal of Fluorine Chemistry , 1992
26.
Fluorocarbon Derivatives. II. Cyclic Nitrides
Simmons T.C., Hoffmann F.W., Beck R.B., Holler H.V., Katz T., Koshar R.J., Larsen E.R., Mulvaney J.E., Paulson K.E., Rogers F.E., Singleton B., Sparks R.E.
Journal of the American Chemical Society , 1957
28.
338. Heterocyclic polyfluoro-compounds. Part I. Pentafluoropyridine
Banks R.E., Ginsberg A.E., Haszeldine R.N.
Journal of the Chemical Society (Resumed) , 1961
29.
29
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
31.
31
A. A. Krasnovskii
Biokhimiya , 1960
32.
32
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
33.
33
M. B. Neiman
"Issledovanie Mekhanizma Okisleniya Butana" (Research on the Mechanism of the Oxidation of Butane) , 1939
34.
Reactions of trifluoroamine oxide: a route to acyclic and cyclic fluoroamines and N-nitrosoamines
Gupta O.D., Kirchmeier R.L., Shreeve J.M.
Journal of the American Chemical Society , 1990
35.
Polymeric analogues of electrophilic fluorinating agents of the N-F class
Banks R.E., Tsiliopoulos E.
Journal of Fluorine Chemistry , 1986
36.
1-Fluoro-2-pyridone: a useful fluorinating reagent
Purrington S.T., Jones W.A.
Journal of Organic Chemistry , 1983
37.
Selective flourinations with 1-flouro-2-pyridone
Purrington S.T., Jones W.A.
Journal of Fluorine Chemistry , 1984
38.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
39.
Specific synthesis of N-fluoro-compounds using perfluorofluoroxy-reagents
Barton D.H., Hesse R.H., Pechet M.M., Toh H.T.
Journal of the Chemical Society Perkin Transactions 1 , 1974
41.
41
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1950
42.
42
L. K. Obukhova
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
44.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
45.
45
W. Hendrich
Roczniki Chemii , 1958
46.
N-Fluoro-N-alkylsulfonamides: useful reagents for the fluorination of carbanions
Barnette W.E.
Journal of the American Chemical Society , 1984
47.
47
G. Oster
"Research in Photosynthesis" , 1957
48.
48
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
49.
49
A. A. Krasnovskii
Biofizika , 1958
50.
50
G. Glacomello
Gazzetta. , 1935
51.
Action de CF3OF sur des aziridines N-substituees
Seguin M., Adenis J.C., Michaud C., Basselier J.J.
Journal of Fluorine Chemistry , 1980
53.
N-fluoro-bis(trifluoromethanesulfonyl) imide. An improved synthesis
Desmarteau D.D., Witz M.
Journal of Fluorine Chemistry , 1991
54.
Synthesis of CF bonds: the pioneering years, 1835 – 1940
Banks R.E., Tatlow J.C.
Journal of Fluorine Chemistry , 1986
55.
55
G. A. Bogdanovskii
1958
56.
56
T. Iasui
Bull. Chem. Soc. Japan. , 1935
57.
57
R. Livingston
"Research in Photosynthesis" , 1957
58.
Fluor in der organischen Synthese
Bohlmann R.
Nachrichten aus Chemie Technik und Laboratorium , 1990
59.
Stereospecific synthesis of alkenyl fluorides (with retention) via organometallic intermediates
Lee S.H., Schwartz J.
Journal of the American Chemical Society , 1986
61.
61
A. N. Terenin
1959
62.
62
A. A. Krasnovskii
"Sbornik, Voprosy Khimicheskoi Kinetiki" (Symposium, Problems of Chemical Kinetics) , 1955
63.
Electrophilic fluorinating agents of the N-F class
Khazei A., Murtagh V., Sharif I., Banks R.E.
Journal of Fluorine Chemistry , 1989
64.
64
Chem. Zentr. II , 1931
65.
65
A. A. Krasnovskii
Biofizika , 1959
66.
Direct fluorination of amides
Grakauskas V., Baum K.
Journal of Organic Chemistry , 1970
67.
N-Fluoro lactams: rapid, mild, and regiospecific fluorinating agents
Satyamurthy N., Bida G.T., Phelps M.E., Barrio J.R.
Journal of Organic Chemistry , 1990
68.
Synthesis and characterization of N-fluoroalkylsulfonamides
Aleinikov N.N., Kondratenko N.V., Kashtanov S.A., Kuntzevich A.D.
Journal of Fluorine Chemistry , 1992
69.
69
B. Commoner
1958
70.
70
N. Bubnov
Biofizika , 1960
71.
71
Yu. A. Shlyapnikov
Vysokomol. Soed. , 1962
72.
72
A. F. Lukovnikov
"Starenie i Stabilizatsiya Polimerov" (Aging arid Stabilisation of Polymers) , 1963
73.
73
T. Skwarski
Chem. Abs. , 1957
74.
74
F. F. Litvin
Uspekhi Fiz. Nauk , 1960
75.
N-Fluoroperfluoroalkylsulfonimides. Remarkable new fluorination reagents
Singh S., DesMarteau D.D., Zuberi S.S., Witz M., Huang H.N.
Journal of the American Chemical Society , 1987
78.
78
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
79.
79
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
80.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1937
81.
81
J. C. Ghosh
J. Indian Chem. Soc. , 1934
82.
82
G. P. Brin
Biokhimiya , 1957
83.
83
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
86.
: Novel reagents for mild and regioselective radiofluorination
Satyamurthy N., Bida G.T., Phelps M.E., Barrio J.R.
International Journal of Radiation Applications and Instrumentation Part A Applied Radiation and Isotopes , 1990
87.
87
J. F. Arens
"Advances in Organic Chemistry" , 1960
88.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1946
89.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow , 1955
90.
90
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1951
91.
91
L. M. Vorob'eva
Biokhimiya , 1956
92.
92
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
93.
Selective, Electrophilic Fluorinations Using N-Fluoro-o-benzenedisulfonimide
Davis F.A., Han W., Murphy C.K.
Journal of Organic Chemistry , 1995
94.
94
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
97.
N-fluoro perfluoroalkylsulphonimides: efficient reagents for the fluorination of 1,3-dicarbonyl derivatives
Xu Z., DesMarteau D.D., Gotoh Y.
Journal of the Chemical Society Chemical Communications , 1991
98.
Electrophilic fluorination of pharmacologically active 1,3-dicarbonyl compounds
Resnati G., DesMarteau D.D.
Journal of Organic Chemistry , 1992
100.
100
V. V. Zolotarev
Chem. Abs. , 1941
102.
Directed ortho metalation - mediated F+ introduction. Regiospecific synthesis of fluorinated aromatics
Snieckus V., Beaulieu F., Mohri K., Han W., Murphy C.K., Davis F.A.
Tetrahedron Letters , 1994
104.
104
O. P. Osipova
Dokl. Akad. Nauk SSSR , 1950
105.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR , 1958
106.
10.1016/00404-0399(50)0892G-
107.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. , 1961
109.
Synthesis of a novel fluoro-tribactam utilising an N-fluorosulfonimide in the key step
Padova A., Roberts S.M., Donati D., Marchioro C., Perboni A.
Tetrahedron , 1996
110.
Synthesis of 3-fluoro azetidinone by electrophilic fluorination
Genêt J., Durand J., Roland S., Savignac M., Jung F.
Tetrahedron Letters , 1997
112.
112
A. G. Pozdeeva
Zhur. Prikl. Khim. , 1952
113.
113
H. Blum
"Photodynamic Action and Diseases caused Light" , 1940
114.
A convenient one-pot synthesis of α-fluoro-α,β-unsaturated nitriles from diethyl cyanofluoromethanephosphonate
Xu Z., DesMarteau D.D.
Journal of the Chemical Society Perkin Transactions 1 , 1992
117.
Electrophilic Fluorination of a Highly Functionalized Pyrrole
Barnes K.D., Hu Y., Hunt D.A.
Synthetic Communications , 1994
121.
ASYMMETRIC SYNTHESIS OF SULTAMS AND SULFONAMIDES VIA DIASTEREOSELECTIVE REDUCTION OF N-SULFONYLIMINES
Davis F.A., Zhou P., Chen B.
Phosphorus, Sulfur and Silicon and the Related Elements , 1996
122.
Asymmetric Fluorination of Enolates with Nonracemic N-Fluoro-2,10-Camphorsultams
Davis F.A., Zhou P., Murphy C.K., Sundarababu G., Qi H., Han W., Przeslawski R.M., Chen B., Carroll P.J.
Journal of Organic Chemistry , 1998
123.
Fluorinated Heterocycles: Targets in the Search for Bioactive Compounds and Tools for their Preparation
Differding E., Frick W., Lang R.W., Martin P., Schmit C., Veenstra S., Greuter H.
Bulletin des Sociétés Chimiques Belges , 2010
124.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
125.
125
K. A. Andrianov
Vysokomol. Soed. , 1960
127.
127
R. Pasternak
Helv. Chim. Acta , 1948
128.
128
J. Wiemann
Bull. Soc. chim. France , 1952
130.
Selective mono- and difluorination of enolates
Differding E., Rüegg G.M., Lang R.W.
Tetrahedron Letters , 1991
132.
132
G. Shima
Kyoto Univ. , 1929
134.
Direct fluorination of substituted pyridines
Van Der Puy M.
Tetrahedron Letters , 1987
135.
Über die Reaktion von Fluor mit Pyridin
Meinert H.
Zeitschrift für Chemie , 2010
138.
Syntheses and Properties ofN-Fluoropyridinium Salts
Umemoto T., Harasawa K., Tomizawa G., Kawada K., Tomita K.
Bulletin of the Chemical Society of Japan , 1991
140.
N-fluoropyridinium pyridine heptafluorodiborate: a useful fluorinating agent
Poss A.J., Van der Puy M., Nalewajek D., Shia G.A., Wagner W.J., Frenette R.L.
Journal of Organic Chemistry , 1991
143.
143
Friedl.
144.
144
1912
145.
145
Friedl.
146.
146
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1952
147.
147
Y. Sasada
Acta Cryst. , 1898
148.
148
P. Kresse
Chem. Abs. , 1960
149.
149
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1954
150.
150
Ya. E. Bernadskaya
"Iskusstvennoe Volokno" (Artificial Fibres) , 1952
151.
Comparison of Commercially Available Reagents for Fluorination of Steroid 3,5-Dienol Acetates
Reydellet-Casey V., Knoechel D.J., Herrinton P.M.
Organic Process Research and Development , 1997
152.
152
W. Albert
Trans. Electrochem. Soc. , 1943
153.
153
1899
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
161.
161
Friedl.
162.
162
1917
163.
163
Friedl.
164.
164
1917
165.
N-F 19-fluorine nuclear magnetic resonance of N-fluoropyridinium salts
Umemoto T., Harasawa K., Tomizawa G., Kawada K., Tomita K.
Journal of Fluorine Chemistry , 1991
166.
166
1917
167.
167
Friedl.
168.
168
1918
169.
169
Friedl.
170.
1-Alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts: a novel family of electrophilic fluorinating agents
Banks R.E., Mohialdin-Khaffaf S.N., Lal G.S., Sharif I., Syvret R.G.
Journal of the Chemical Society Chemical Communications , 1992
171.
171
Friedl.
173.
173
Friedl.
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.
179
Chem. Abs. , 1947
181.
181
Chem. Abs. , 1947
182.
Novel base-initiated reactions of N-substituted pyridinium salts
Umemoto T., Tomizawa G., Hachisuka H., Kitano M.
Journal of Fluorine Chemistry , 1996
183.
183
Chem. Abs. , 1947
184.
Derivatives of N-Fluoropyridinium Salt
NUKUI K.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry , 1995
185.
Power- and structure-variable fluorinating agents. The N-fluoropyridinium salt system
Umemoto T., Fukami S., Tomizawa G., Harasawa K., Kawada K., Tomita K.
Journal of the American Chemical Society , 1990
186.
186
Chem. Abs. , 1956
187.
187
1954
188.
Controlled selective fluorination with N-fluoropyridinium salt system
Tomizawa G., Umemoto T.
Journal of Fluorine Chemistry , 1991
189.
189
M. Godchot
Bull. Soc. chim. France (5) , 1913
190.
190
H. Law
J. Chem. Soc. , 1912
191.
Enantioselective synthesis of monofluorinated chiral building blocks from malonic acid
Ihara M., Kai T., Taniguchi N., Fukumoto K.
Journal of the Chemical Society Perkin Transactions 1 , 1990
194.
194
A. A. Vertman
"Svoistva Rasplavov Zheleza" (Properties of Iron Melts) , 1969
195.
195
M. Allen
J. Chem. Soc. , 1961
196.
196
E. Müller
Z. Elektrochem. , 1910
197.
197
J. Sicher
Chem. Listy , 1955
198.
198
W. Cohen
Rec. Trav. chim. , 1919
199.
Enantioselective construction of quaternary stereogenic centres possessing a fluorine atom
Ihara M., Taniguchi N., Kai T., Satoh K., Fukumoto K.
Journal of the Chemical Society Perkin Transactions 1 , 1992
200.
200
Ref. Zh. Khim. , 1975
201.
201
A. Aladjem
1969
203.
α-Fluorination of Sulfides withN-Fluoropyridinium Triflates
Umemoto T., Tomizawa G.
Bulletin of the Chemical Society of Japan , 1986
206.
Time-resolved spectroscopy and charge-transfer photochemistry of aromatic EDA complexes with X-pyridinium cations
Bockman T.M., Lee K.Y., Kochi J.K.
Journal of the Chemical Society Perkin Transactions 2 , 1992
207.
Structural effects controlling the rate of the retro-Diels-Alder reaction in anthracene cycloadducts
Chung Y., Duerr B.F., McKelvey T.A., Nanjappan P., Czarnik A.W.
Journal of Organic Chemistry , 1989
208.
Charge-transfer structures of aromatic EDA complexes with N-heteroatom-substituted pyridinium cations
Lee K.Y., Kochi J.K.
Journal of the Chemical Society Perkin Transactions 2 , 1992
210.
Efficient regioselective a-ring functionalization of oestrogens
Bulman Page P.C., Hussain F., Maggs Paul Morgan J.L., Kevin Park B.
Tetrahedron , 1990
211.
211
C. Schall
Z. Elektrochem. , 1923
212.
212
L. V. Pavlova
Zh. Obshch. Khim. , 1965
214.
Synthesis and Properties of Fluoroazulenes. II. Electrophilic Fluorination of Azulenes withN-Fluoro Reagents
Ueno T., Toda H., Yasunami M., Yoshifuji M.
Bulletin of the Chemical Society of Japan , 1996
215.
N-halogeno compounds. Part 9. N-Fluoroquinuclidinium fluoride—a new electrophilic fluorinating agent
Banks R.E., Du Boisson R.A., Morton W.D., Tsiliopoulos E.
Journal of the Chemical Society Perkin Transactions 1 , 1988
216.
216
A. P. Tomilov
Zhur. Prikl. Khim. , 1959
217.
217
1925
218.
N-halogeno-compounds. Parts 10. N-fluoroquinuclidinium triflate
Banks R.E., Sharif I.
Journal of Fluorine Chemistry , 1988
220.
220
K. Ziegler
Angew. Chem. , 1955
221.
221
1960
223.
Electrophilic fluorination with N-fluoroquinuclidinium fluoride
Banks R.E., Du Boisson R.A., Tsiliopoulos E.
Journal of Fluorine Chemistry , 1986
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.
233
P. Cotter
J. Am. Chem. Soc. , 1956
233.
234
Ebach E A
Chem. Abs. , 1966
234.
235
R. Peffen
1967
235.
236
P. Peshev
Rev. internat. hautes Temperat. et Réfract. , 1969
236.
A new method for the electrophilic fluorination of vinyl stannanes
Matthews D.P., Miller S.C., Jarvi E.T., Sabol J.S., McCarthy J.R.
Tetrahedron Letters , 1993
237.
N-Fluoroquinuclidinium trifluoromethanesulfonate (triflate): a novel electrophilic fluorinating agent
Banks R.E., Pritchard R.G., Sharif I.
Acta Crystallographica Section C Crystal Structure Communications , 1993
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
243.
1,4-Difluoro-1,4-diazoniabicyclo [2.2.2] octane salts
Banks R.E., Besheesh M.K.
Journal of Fluorine Chemistry , 1995
244.
A new, selective method for conversion of alcohols to vicinal fluorohydrins
Stavber S., Zupan M.
Journal of the Chemical Society Chemical Communications , 1994
245.
246
G. A. Meerson
Byull. Izobr. , 1968
247.
Regiospecific synthesis of 4-fluoro-Δ4,3-keto steroids using caesium fluoroxysulfate
Hodson H.F., Madge D.J., Widdowson D.A.
Journal of the Chemical Society Perkin Transactions 1 , 1995
248.
249
A. I. Fedorova
Dokl. Akad. Nauk SSSR , 1961
249.
Electrophilic fluorination in the synthesis of new fluoroindoles
Hodson H.F., Madge D.J., Slawin A.N., Widdowson D.A., Williams D.J.
Tetrahedron , 1994
251.
Solvent effects in the fluorination of aromatic molecules with ‘F-TEDA-BF4’
Zupan M., Iskra J., Stavber S.
Journal of Fluorine Chemistry , 1995
254.
255
Tomita M
Chem. Abs. , 1939
255.
5-Fluorocyclopentadiene: synthesis and utility
McClinton M.A., Sik V.
Journal of the Chemical Society Perkin Transactions 1 , 1992
256.
Stereochemistry and Some Kinetic Aspects of Fluorination of Phenyl-Substituted Alkenes with SelectfluorTMReagent F-TEDA-BF4
Stavber S., Sotler-Pecan T., Zupan M.
Bulletin of the Chemical Society of Japan , 1996
258.
259
V. Elyutin
Trudy Moskov. Inst. Stali , 1939
260.
Synthesis of 2-fluorotetronic acid
Ge P., Kirk K.L.
Journal of Fluorine Chemistry , 1997
261.
Synthesis of 2-Deoxy-2-halo-l-ascorbic Acids
Ge P., Kirk K.L.
Journal of Organic Chemistry , 1997
263.
Mild α-fluorination of enantiomerically pure β-ketosulfoxides by F-TEDA-BF4
Arnone A., Bravo P., Frigerio M., Salani G., Viani F., Zanda M., Zappalà C.
Journal of Fluorine Chemistry , 1997
264.
265
E. A. Ostroumov
Zavod. Lab. , 1935
265.
Synthesis of fluorinated azulenes
Muthyala R.S., Liu R.S.
Journal of Fluorine Chemistry , 1998
271.
272
J. Johnston
Edin. J. Sci. (New Ser.) , 1831
272.
273
J. Johnston
Edin. J. Sci. (New Ser.) , 1831
273.
274
J. Johnston
Edin. J. Sci. (New Ser.) , 1831
274.
275
H. Moissan
Compt. rend. , 1895
275.
Reactions of the N-F class of fluorinating reagents with solvents
Zupan M., Papez M., Stavber S.
Journal of Fluorine Chemistry , 1996
277.
278
L. Troost
Compt. rend. , 1865
278.
279
B. de Jassonneix
Compt. rend. , 1906
280.
281
B. de Jassonneix
Compt. rend. , 1906
281.
282
B. de Jassonneix
Compt. rend. , 1906
282.
283
H. Moissan
Compt. rend. , 1902
283.
284
H. Moissan
Compt. rend. , 1902
284.
285
Emanuel' N M
Dokl. Akad. Nauk SSSR , 1974
285.
286
W. Schedler
1902
286.
Improved syntheses of NF4BF4 and NF4SbF6
Christe K.O., Schack C.J., Wilson R.D.
Journal of Fluorine Chemistry , 1976
287.
Substitution and addition reactions of NF4BF4 with aromatic compounds
Schack C.J., Christe K.O.
Journal of Fluorine Chemistry , 1981
288.
289
Kopylov V V
Symposium, "Anilino-Krasochnaya Promyshlennost'" (The Aniline Dye Industry) , 1970
289.
290
Guntz
Compt. rend. , 1902
290.
291
Ya. S. Umanskii
Zh. Fiz. Khim. , 1940
291.
292
Pechernikova Z P
Zavod. Lab. , 1978
292.
293
Wattenberg L W
J. Nat. Cancer Inst. , 1972
293.
294
H. I. Schlesinger
J. Am. Chem. Soc. , 1937
294.
295
Burlakova E B
Dokl. Akad. Nauk SSSR , 1965
295.
296
H. I. Schlesinger
J. Am. Chem. Soc. , 1940
298.
Electron Transfer Reactions in Organic Chemistry
Eberson L.
Reactivity and Structure: Concepts in Organic Chemistry , 1987
299.
300
P. P. Alexander
Chem. Abs. , 1949
300.
301
N. Razkazov
"Metalokeramika Spets. Splavi i Kontaktni Materiali" (Powder Metallurgy, Special Alloys, and Contact Materials) , 1967
301.
302
N. Razkazov
1969
302.
303
Emanuel' N M
Izv. Akad. Nauk SSSR, Ser. Biol. , 1975
303.
Mo studies of solvation effects
Burshtein K.Y.
Journal of Molecular Structure THEOCHEM , 1987
304.
On the relative power of electrophilic fluorinating reagents of the NF class
Gilicinski A.G., Pez G.P., Syvret R.G., Lal G.S.
Journal of Fluorine Chemistry , 1992
306.
307
Y. Doi
Chem. Abs. , 1968
307.
Synthesis, characterization, and applications of new electrophilic fluorinating agents of the NF class
Banks R.E., Besheesh M.K., Khaffaf S.N., Sharif I.
Journal of Fluorine Chemistry , 1991
308.
309
E. Clar
1969
309.
310
R. Paris
Chimie et Industrie , 1969
310.
311
L. A. Dvorina
Zh. Prikl. Khim. , 1968