Home / Articles / [3,3]-Sigmatropic rearrangements as a method of organofluorine synthesis

[3,3]-Sigmatropic rearrangements as a method of organofluorine synthesis

V G Andreev 1
V G Andreev
, 
Aleksei Filippovich Kolomiets 1
Aleksei Filippovich Kolomiets
1 A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Moscow
10.1070/RC1993v062n06ABEH000033
Published 30 November 1992
Communication , Volume 62, Issue 6, 553-578
7
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Andreev V. G., Kolomiets A. F. [3,3]-Sigmatropic rearrangements as a method of organofluorine synthesis // Russian Chemical Reviews. 1993. Vol. 62. No. 6. pp. 553-578.
GOST all authors (up to 50)
Copy cite
Andreev V. G., Kolomiets A. F. [3,3]-Sigmatropic rearrangements as a method of organofluorine synthesis // Russian Chemical Reviews. 1993. Vol. 62. No. 6. pp. 553-578.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RC1993v062n06ABEH000033
UR - https://rcr.colab.ws/publications/10.1070/RC1993v062n06ABEH000033
TI - [3,3]-Sigmatropic rearrangements as a method of organofluorine synthesis
T2 - Russian Chemical Reviews
AU - Andreev, V G
AU - Kolomiets, Aleksei Filippovich
PY - 1993
DA - 1992/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 553-578
IS - 6
VL - 62
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{1993_Andreev,
author = {V G Andreev and Aleksei Filippovich Kolomiets},
title = {[3,3]-Sigmatropic rearrangements as a method of organofluorine synthesis},
journal = {Russian Chemical Reviews},
year = {1993},
volume = {62},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1993v062n06ABEH000033},
number = {6},
pages = {553--578},
doi = {10.1070/RC1993v062n06ABEH000033}
}
MLA
Cite this
MLA
Copy cite
Andreev, V. G., and Aleksei Filippovich Kolomiets. “[3,3]-Sigmatropic rearrangements as a method of organofluorine synthesis.” Russian Chemical Reviews, vol. 62, no. 6, Nov. 1993, pp. 553-578. https://rcr.colab.ws/publications/10.1070/RC1993v062n06ABEH000033.
Views / Visits / Downloads
11 / 11 / 3

Abstract

Literature data on [3,3]-sigmatropic rearrangements of organofluorine compounds are surveyed and described systematically in terms of the type of substances and intermediates involved in the rearrangements. The characteristic features of these reactions are considered as a function of the structure of the isomerising molecules and the positions in the latter of fluorine atoms and fluorine-containing substituents. The possibilities arising from the use of the [3,3]-sigmatropic rearrangements for the specific synthesis of fluorine-containing compounds belonging to particular classes are assessed. The bibliography includes 180 references.

References

1.
Über Umlagerung von Phenol-allyläthern in C-Allyl-phenole
Claisen L.
Berichte der deutschen chemischen Gesellschaft , 1912
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. , 1956
3.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) , 1952
4.
Molecular rearrangements related to the Claisen rearrangement
Jefferson A., Scheinmann F.
Quarterly Reviews Chemical Society , 1968
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
7.
シグマトロピー転位を利用する有機合成
HAYASHI T.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry , 1976
11.
Molecular Rearrangements
Murray A.W.
Organic Reaction Mechanisms
12.
12
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
13.
Claisen rearrangements in heteroaromatic systems
Moody C.J.
Advances in Heterocyclic Chemistry , 1987
14.
The thermal, aliphatic Claisen rearrangement
Ziegler F.E.
Chemical Reviews , 1988
15.
Allylic and propargylic imidic esters in organic synthesis
Overman L.E.
Accounts of Chemical Research , 1980
16.
THE THIO-CLAISEN REARRANGEMENT
Morin L., Lebaud J., Paquer D., Chaussin R., Barillier D.
Phosphorous and Sulfur and the Related Elements , 1979
17.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
18.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
19.
The Cope Aza-rearrangement in Organic Synthesis
Przheval'skii N.M., Grandberg I.I.
Russian Chemical Reviews , 1987
21.
The Conservation of Orbital Symmetry
Woodward R.B., Hoffmann R.
Angewandte Chemie - International Edition , 1969
22.
Stereochemical Control Through Sigmatropic Rearrangements
NAKAI T., MIKAMI K., SAYO N.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry , 1983
25.
26
B. Ya. Dain
1957
27.
28
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
28.
Synthetic approach to natural products by Claisen rearrangement of glyceraldehyde derivatives
Kametani T., Kasai H., Sato E., Suzuki T.
Proceedings of the Indian Academy of Sciences - Section A , 1988
29.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
30.
31
A. A. Krasnovskii
Biokhimiya , 1960
31.
32
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
32.
33
M. B. Neiman
"Issledovanie Mekhanizma Okisleniya Butana" (Research on the Mechanism of the Oxidation of Butane) , 1939
34.
Carbanion-accelerated Claisen rearrangements
Denmark S.E., Harmata M.A.
Journal of the American Chemical Society , 1982
37.
Carbanion-accelerated Claisen rearrangements. 6. Preparative and stereochemical studies with sulfonyl-stabilized anions
Denmark S.E., Harmata M.A., White K.S.
Journal of the American Chemical Society , 1989
39.
Ground states of molecules. 68. MNDO study of the Claisen rearrangement
Dewar M.J., Healy E.F.
Journal of the American Chemical Society , 1984
42.
[3,3]-Sigmatropic rearrangements of fluorocarbanions
Andreev V.G., Kolomiets A.F., Fokin A.V.
Journal of Fluorine Chemistry , 1992
43.
[3,3]-Sigmatropic rearrangements of fluorinated compounds
Purrington S.T., Weeks S.C.
Journal of Fluorine Chemistry , 1992
44.
Fluor-, chlor- und jodbullvalen
Oth J.F., Merényi R., Röttele H., Schröder G.
Tetrahedron Letters , 1968
45.
Tetrakis(trifluoromethyl)semibullvalenes. Could Cope degeneration be frozen out?
Kobayashi Y., Ando A., Kawada K., Kumadaki I.
Journal of the American Chemical Society , 1981
48.
Electronic aspect of face selection in the oxy-Cope rearrangement
Lin M.H., Le Noble W.J.
Journal of Organic Chemistry , 1989
60.
61
A. N. Terenin
1959
61.
Polyhalogenoaromatic compounds. Part 40. Synthesis and thermal rearrangements of some polychloropyridines
Iddon B., Suschitzky H., Taylor J.A.
Journal of the Chemical Society Perkin Transactions 1 , 1979
63.
Sigmatropic shifts with polyflouroaromatic compounds
Brooke G.M., Cooperwaite J.R., Ferguson J.A., Morpeth A.G.
Journal of Fluorine Chemistry , 1985
68.
Formation of tropolone derivatives (2H-cyclohepta[b]furan-2-ones) by the pyrolysis of aryl propiolates
Trahanovsky W.S., Emeis S.L., Lee A.S.
Journal of Organic Chemistry , 1976
70.
71
Yu. A. Shlyapnikov
Vysokomol. Soed. , 1962
73.
74
F. F. Litvin
Uspekhi Fiz. Nauk , 1960
76.
A New Synthesis of 3-Fluoroveratrole and 2-Fluoro-3, 4-Dimethoxybenzaldehyde
Ladd D.L., Gaitanopoulos D., Weinstock J.
Synthetic Communications , 1985
78.
Lewis acid-mediated Claisen-type rearrangement of aryl dienyl ethers
Maruyama K., Nagai N., Naruta Y.
Journal of Organic Chemistry , 1986
79.
A novel reaction between acetone and the benzo[c]phenanthrene K-region o-quinone containing a peri-fluoro substituent
Patrick M.A., Sethi S.K., Unger S.E., Mirsadeghi S., Ribeiro A.A., Thakker D.R.
Journal of Organic Chemistry , 1991
80.
Claisen Rearrangement of Allyl 3-(Trifluoromethyl)-phenyl Ether
McBee E.T., Rapkin E.
Journal of the American Chemical Society , 1951
81.
Claisen rearrangement of meta-substituted allyl phenyl ethers
Bruce J.M., Roshan-Ali Y.
Journal of the Chemical Society Perkin Transactions 1 , 1981
83.
Umlagerung von Allyl‐aryläthern und Allyl‐cyclohexadienonen mittels Bortrichlorid
Borgulya J., Madeja R., Fahrni P., Hansen H., Schmid H., Barner R.
Helvetica Chimica Acta , 1973
84.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
85.
86
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
86.
87
J. F. Arens
"Advances in Organic Chemistry" , 1960
87.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1946
88.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow , 1955
89.
90
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1951
90.
91
L. M. Vorob'eva
Biokhimiya , 1956
91.
92
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
92.
93
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
94.
95
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
95.
A novel synthetic route to α-trifluoromethyl substituted α-amino acids
Burger K., Gaa K., Geith K.
Journal of Fluorine Chemistry , 1989
96.
97
A. N. Terenin
Dokl. Akad. Nauk SSSR , 1952
100.
101
M. F. Shostakovskii
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
101.
Synthesis and reaction behaviour of 2-fluoro-3-trifluoromethyl substituted furans and thiophens
Helmreich B., Jendrewski O., Burger K.
Journal of Fluorine Chemistry , 1992
105.
106
F. Fichter
Helv. Chim. Acta , 1927
106.
Peptide modification by introduction of α-trifluoromethyl substituted α-amino acids
Mütze K., Hollweck W., Burger K.
Journal of Fluorine Chemistry , 1992
107.
Thermal rearrangements of gem-difluorocyclopropanes
Dolbier W.R.
Accounts of Chemical Research , 1981
108.
On the nature of the perfluoroalkyl (Rf) effect
Greenberg A., Liebman J.F., Van Vechten D.
Tetrahedron , 1980
109.
The synthesis of α,α-difluoroaldehydes and ketones via claisen rearrangements
Metcalf B.W., Jarvi E.T., Burkhart J.P.
Tetrahedron Letters , 1985
111.
Stereospecific synthesis of (±)-fluorobotryodiplodin
Nakahara Y., Shimizu M., Yoshioka H.
Tetrahedron Letters , 1988
112.
113
H. Blum
"Photodynamic Action and Diseases caused Light" , 1940
113.
114
L. Segal
"Chemical Reactions of Polymers" , 1964
115.
The mechanism of rearrangement of chorismic acid and related compounds
Gajewski J.J., Jurayj J., Kimbrough D.R., Gande M.E., Ganem B., Carpenter B.K.
Journal of the American Chemical Society , 1987
116.
117
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
117.
118
V. M. Rodionov
Zhur. Obshch. Khim. , 1935
118.
119
V. V. Levchenko
Zhur. Obshch. Khim. , 1947
119.
Hexafluoropropene trimer. Synthesis and properties of functional derivatives
Makarov K.N., Gervits L.L., Cheburkov Y.A., Knunyants I.L., Sass V.P.
Journal of Fluorine Chemistry , 1977
120.
121
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
121.
122
S. R. Rafikov
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
122.
The Valence Isomerization of 1,2-Divinylaziridines. Synthetic and Kinetic Studies
Stogryn E.L., Brois S.J.
Journal of the American Chemical Society , 1967
123.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
124.
125
K. A. Andrianov
Vysokomol. Soed. , 1960
125.
126
J. Wiemannand Ch. Clachet
Compt. rend. , 1948
126.
127
R. Pasternak
Helv. Chim. Acta , 1948
127.
128
J. Wiemann
Bull. Soc. chim. France , 1952
128.
The Chemistry of Perfluoroisobutene
Zeifman Y.V., Ter-Gabrielyan E.G., Gambaryan N.P., Knunyants I.L.
Russian Chemical Reviews , 1984
129.
Reactions of Polyfluoro Olefins. III.1 Preparation of Polyfluoro Ethers2
Barr J.T., Rapp K.E., Pruett R.L., Bahner C.T., Gibson J.D., Lafferty R.H.
Journal of the American Chemical Society , 1950
130.
131
N. Thooi
Compt. rend. , 1958
132.
133
C. Wilson
Trans. Electrochem. Soc. , 1941
133.
134
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1948
134.
Synthesis and evaluation of phospholipid analogs as inhibitors of cobra venom phospholipase A2
Yuan W., Berman R.J., Gelb M.H.
Journal of the American Chemical Society , 1987
135.
Nucleophilic Reactions of Fluoroölefins
England D.C., Melby L.R., Dietrich M.A., Lindsey R.V.
Journal of the American Chemical Society , 1960
136.
137
S. R. Rafikov
Zh. Obshch. Khim. , 1944
138.
139
I. L. Knunyants
1959
139.
Reactions of halothane under phase-transfer conditions
Radchenko O.A., Il'chenko A.Y.
Journal of Fluorine Chemistry , 1992
140.
141
Friedl.
141.
142
1913
143.
144
1912
144.
145
Friedl.
145.
The Addition of Alcohols to Octafluoroisobutene1
Koshar R.J., Simmons T.C., Hoffmann F.W.
Journal of the American Chemical Society , 1957
146.
147
Y. Sasada
Acta Cryst. , 1898
147.
148
P. Kresse
Chem. Abs. , 1960
148.
Synthesis of monofluorinated compounds from methallyl chloride
Haufe G., Schulze K., Alvernhe G.
Journal of Fluorine Chemistry , 1991
149.
150
Ya. E. Bernadskaya
"Iskusstvennoe Volokno" (Artificial Fibres) , 1952
151.
152
W. Albert
Trans. Electrochem. Soc. , 1943
152.
Direct observation of simple fluorinated carbanions
Bayliff A.E., Bryce M.R., Chambers R.D., Matthews R.S.
Journal of the Chemical Society Chemical Communications , 1985
153.
154
Friedl.
154.
155
M. V. Mal'tsev
Izv. Vys. Ucheb. Zaved., Tsvet. Met. , 1960
155.
156
J. S. Fruton
J. Biol. Med. , 1950
156.
157
1903
157.
158
Friedl.
158.
159
J. Tafel
Z. Elektrochem. , 1911
160.
161
Friedl.
161.
162
1917
162.
163
Friedl.
163.
164
1917
164.
165
Friedl.
165.
166
1917
166.
167
Friedl.
168.
169
Friedl.
169.
170
1918
170.
171
Friedl.
171.
172
1918
174.
175
I. Mayer
1966
175.
Nucleophilic reactions of 4-perfluoroalkylthiotetrachloropyridines
Sipyagin A.M., Paltsun S.V., Pomytkin I.A., Aleinikov N.N.
Journal of Fluorine Chemistry , 1992
176.
177
J. Henry
Proc. R. Irish Acad. , 1945
177.
The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation
Ireland R.E., Mueller R.H., Willard A.K.
Journal of the American Chemical Society , 1976
178.
179
Chem. Abs. , 1947
179.
Facile diastereoselective ester enolate Claisen rearrangements of allyl fluoroacetates
Welch J.T., Samartino J.S.
Journal of Organic Chemistry , 1985
180.
Ester enolate Claisen rearrangements of allyl .alpha.-fluoroacetates and .alpha.-fluoropropanoates
Welch J.T., Plummer J.S., Chou T.S.
Journal of Organic Chemistry , 1991
181.
182
1947
182.
Stereocontrolled syntheses of fluorinated synthons and their application to the preparation of fluorinated sugars
Araki K., Plummer J.S., Gyenes F., O'Toole J., Welch J.T.
Journal of Fluorine Chemistry , 1991
184.
185
1954
185.
186
Chem. Abs. , 1956
186.
Fluorine-containing organozinc reagents. V.
Greuter H., Lang R.W., Romann A.J.
Tetrahedron Letters , 1988
189.
An accelerated diastereoselective variant of the amide acetal Claisen rearrangement
Welch J.T., Eswarakrishnan S.
Journal of Organic Chemistry , 1985
191.
Regioselective aza-Cope rearrangement of .alpha.-halogenated and nonhalogenated imines
Welch J.T., De Corte B., De Kimpe N.
Journal of Organic Chemistry , 1990
192.
Insect chemistry IV. Trifluoromethyl analogs of juvenile hormones
Camps F., Coll J., Messeguer A., Roca A.
Tetrahedron Letters , 1976
193.
Insect chemistry—VI
Camps F., Canela R., Coll J., Messeguer A., Roca A.
Tetrahedron , 1978
195.
Simple stereoselective version of the Claisen rearrangement leading to trans-trisubstituted olefinic bonds. Synthesis of squalene
Johnson W.S., Werthemann L., Bartlett W.R., Brocksom T.J., Li T., Faulkner D.J., Petersen M.R.
Journal of the American Chemical Society , 1970
196.
SYNTHESES OF β, β-DIFLUOROCARBOXYLIC ACID DERIVATIVES THROUGH THE CLAISEN REARRANGEMENT OF 1, 1-DIFLUORO-1-ALKEN-3-OLS
Taguchi T., Morikawa T., Kitagawa O., Mishima T., Kobayashi Y.
Chemical and Pharmaceutical Bulletin , 2017
197.
198
W. Cohen
Rec. Trav. chim. , 1919
198.
Stereoselective synthesis of trifluoromethylated olefin and diene.
Hanzawa Y., Kawagoe K., Kimura N., Kobayashi Y.
Chemical and Pharmaceutical Bulletin , 2011
199.
Fluorinated retinoic acids and their analogs. 1. Synthesis and biological activity of (4-methoxy-2,3,6-trimethylphenyl)nonatetraenoic acid analogs
Pawson B.A., Chan K., DeNoble J., Han R.J., Piermattie V., Specian A.C., Srisethnil S., Trown P.W., Bohoslawec O.
Journal of Medicinal Chemistry , 1979
201.
202
G. Shiroa
Mem. Coll. Sci., Kyoto Univ. , 1930
202.
Polymer chemistry. Part 1. Model compounds related to hexafluoropropenevinylidene fluoride elastomer
Aspey G.C., Chambers R.D., Salisbury M.J., Moggi G.
Journal of Fluorine Chemistry , 1988
203.
204
Cherkesov A I
Ref. Zh. Khim. , 1968
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.
Electronic control of face selection in the [3,3] sigmatropic rearrangement of allyl vinyl sulfoxides
Mukherjee A., Schulman E.M., Le Noble W.J.
Journal of Organic Chemistry , 1992
209.
Perfluorodiazo Compounds
Gale D.M., Middleton W.J., Krespan C.G.
Journal of the American Chemical Society , 1966