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S-Cationoid reagents in organic synthesis

Ivan Vasil'evich Koval' 1
Ivan Vasil'evich Koval'
1 Ukrainian University of Chemical Engineering, Dnepropetrovsk
10.1070/RC1995v064n02ABEH000142
Published 30 November 1994
Communication , Volume 64, Issue 2, 141-166
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Koval' I. V. S-Cationoid reagents in organic synthesis // Russian Chemical Reviews. 1995. Vol. 64. No. 2. pp. 141-166.
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Koval' I. V. S-Cationoid reagents in organic synthesis // Russian Chemical Reviews. 1995. Vol. 64. No. 2. pp. 141-166.
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TY - JOUR
DO - 10.1070/RC1995v064n02ABEH000142
UR - https://rcr.colab.ws/publications/10.1070/RC1995v064n02ABEH000142
TI - S-Cationoid reagents in organic synthesis
T2 - Russian Chemical Reviews
AU - Koval', Ivan Vasil'evich
PY - 1995
DA - 1994/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 141-166
IS - 2
VL - 64
ER -
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@article{1995_Koval',
author = {Ivan Vasil'evich Koval'},
title = {S-Cationoid reagents in organic synthesis},
journal = {Russian Chemical Reviews},
year = {1995},
volume = {64},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1995v064n02ABEH000142},
number = {2},
pages = {141--166},
doi = {10.1070/RC1995v064n02ABEH000142}
}
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Koval', Ivan Vasil'evich. “S-Cationoid reagents in organic synthesis.” Russian Chemical Reviews, vol. 64, no. 2, Nov. 1995, pp. 141-166. https://rcr.colab.ws/publications/10.1070/RC1995v064n02ABEH000142.
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Abstract

The review is devoted to the methods of preparation, properties and applications in organic synthesis of compounds of divalent, tetravalent, and hexavalent sulfur which may bear a positive charge on the sulfur atom, such as sulfenium, sulfonium, and sulfoxonium (oxosulfonium) reagents. The bibliography includes 178 references.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. , 1956
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.
Generation and chemical reactions of episolfonium ions
Smit W.A., Krimer M.Z., Vorob'eva E.A.
Tetrahedron Letters , 1975
8.
Episulfonium ions: myth and reality
Smit V.A., Zefirov N.S., Bodrikov I.V., Krimer M.Z.
Accounts of Chemical Research , 1979
9.
9
V. H. Lynch
Carnegie Inst. Year Book , 1954
10.
DIRECTION OF RING-OPENING OF A THIIRANIUM ION
Oki M., Nakanishi W., Fukunaga M., Smith G.D., Duax W.L., Osawa Y.
Chemistry Letters , 1975
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.
Dimeric cations from alkanesulphenyl chlorides. The elusive nature of sulphenylium ions
Capozzi G., Lucchini V., Modena G., Rivetti F.
Journal of the Chemical Society Perkin Transactions 2 , 1975
15.
15
A. S. Holt
"Research in Photosynthesis" , 1957
16.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
18.
Correlation of the rates of solvolysis of the benzyldiphenylsulfonium ion
Kevill D.N., Ismail N.H.
Journal of Organic Chemistry , 1991
19.
Synthesis of Thiazole-Based DNA-Targeting Molecules Aiming at Guanine Specificity
Kobayashi S., Kuroda R., Watanabe T., Otsuka M.
Synlett , 1992
20.
Dimethyl-α-styrylsulphonium bromide as a reaction intermediate
Chow Y.L., Bakker B.H., Iwai K.
Journal of the Chemical Society Chemical Communications , 1980
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.
25
G. W. Robinson
J. Chem. Phys. , 1955
26.
26
B. Ya. Dain
1957
27.
Diphenylsulfonium cyclopropylide. Useful spiroalkylation reagnet
Trost B.M., Bogdanowicz M.J.
Journal of the American Chemical Society , 1971
28.
28
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
30.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
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.
Photolysis of tris(4-tert-butoxycarbonyloxyphenyl) sulphonium salts. A mechanistic study
Schwalm R., Bug R., Dai G., Fritz P.M., Reinhardt M., Schneider S., Schnabel W.
Journal of the Chemical Society Perkin Transactions 2 , 1991
35.
Wavelength dependence of the photolysis of some anthracene-containing sulfonium salts
He X., Huang W.Y., Reiser A.
Journal of Organic Chemistry , 1992
36.
36
J. Billon
Bull. Soc. chim. France , 1960
37.
37
L. M. Kosobutskaya
Dokl. Akad. Nauk SSSR , 1950
38.
New synthetic methods. Transfer of chirality from sulfur to carbon
Trost B.M., Hammen R.F.
Journal of the American Chemical Society , 1973
39.
39
V. F. Gachkovskii
Biofizika , 1959
43.
43
N. Bunge
Ber. Deutsch. Chem. Ges. , 1870
44.
Laboratory model for the biosynthesis of cyclopropane rings. Copper-catalyzed cyclopropanation of olefins by sulfur ylides
Cohen T., Herman G., Chapman T.M., Kuhn D.
Journal of the American Chemical Society , 1974
45.
New synthetic reactions. Geminal alkylation
Trost B.M., Bogdanowicz M.J.
Journal of the American Chemical Society , 1973
46.
Oxaspiropentanes
Bogdanowicz M.J., Trost B.M.
Tetrahedron Letters , 1972
47.
New synthetic reactions. Cyclopentane annelation
Trost B.M., Bogdanowicz M.J.
Journal of the American Chemical Society , 1973
48.
Perturbation of rearrangement courses by cyclohepta-amylose
Mitani M., Tsuchida T., Koyama K.
Journal of the Chemical Society Chemical Communications , 1974
49.
Asymmetric induction in the Sommelet rearrangement of chiral benzyl sulfonium salts
Campbell S.J., Darwish D.
Canadian Journal of Chemistry , 1976
52.
Elimination and addition reactions. Part 29. Ylide rearrangement in adducts from allenic sulphonium salts and malonic esters
Griffiths G., Howes P.D., Stirling C.J.
Journal of the Chemical Society Perkin Transactions 1 , 1977
53.
Methylides from trimethylsilylmethylsulfonium, -ammonium, -immonium, and -phosphonium salts
Vedejs E., Martinez G.R.
Journal of the American Chemical Society , 1979
54.
54
R. Livingston
J. Phys. Chem. , 1941
55.
55
G. A. Bogdanovskii
1958
56.
Stereoselectivity and carbon-14 isotope effect in methyl group transfer from s-butyldimethylsulphonium to para-thiocresolate ion
Grue-Sørensen G., Kjær A., Wieczorkowska E.
Journal of the Chemical Society Chemical Communications , 1977
57.
57
R. Livingston
"Research in Photosynthesis" , 1957
58.
A New Method of Perfluoroalkylation
YAGUPOLSKII L.M., MALETINA I.I., KONDRATENKO N.V., ORDA V.V.
Synthesis , 1978
59.
59
H. Linshitz
"Research in Photosynthesis" , 1957
60.
New general syntheses for symmetrical and unsymmetrical organic sulphides
Labuschagne A.J., Malherbe J.S., Meyer C.J., Schneider D.F.
Tetrahedron Letters , 1976
61.
61
A. N. Terenin
1959
62.
62
A. A. Krasnovskii
"Sbornik, Voprosy Khimicheskoi Kinetiki" (Symposium, Problems of Chemical Kinetics) , 1955
63.
63
1930
64.
64
Chem. Zentr. II , 1931
65.
65
A. A. Krasnovskii
Biofizika , 1959
66.
66
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
68.
68
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1946
69.
The chemistry of disulfides
Koval' I.V.
Russian Chemical Reviews , 1994
70.
LACTONIZATION REACTIONS OF (ω-CARBOXYALKYL)SULFONIUM SALTS
Nakamura T., Matsuyama H., Takahashi M., Kamigata N.
Phosphorus, Sulfur and Silicon and the Related Elements , 1992
71.
Chemistry of sulfoxides and related compounds. XLIII. Conversion of ketones to epoxides via .beta.-hydroxy sulfides
Shanklin J.R., Johnson C.R., Ollinger J., Coates R.M.
Journal of the American Chemical Society , 1973
72.
Reduction of Sulfonium and Selenonium Salts with Samarium Diiodide
Kataoka T., Iwama T., Shimizu H., Hori M.
Phosphorus, Sulfur and Silicon and the Related Elements , 1992
76.
The chemistry of sulfilimines
Gilchrist T.L., Moody C.J.
Chemical Reviews , 1977
77.
77
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
79.
79
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
80.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1937
81.
Sulfides: synthesis and properties
Koval' I.V.
Russian Chemical Reviews , 1994
82.
N-aryl sulfimides
Claus P.K., Rieder W., Hofbauer P., Vilsmaier E.
Tetrahedron , 1975
83.
83
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
84.
Progress in the chemistry of sulphilimines
Koval' I.V.
Russian Chemical Reviews , 1990
86.
86
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
87.
Concerning the preparation of monofluorinated sulfonium salts
Bäck B., Minkwitz R., Nowicki G.
Journal of Fluorine Chemistry , 1991
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.
93
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
94.
94
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
96.
98
W. Franke
Chem. Zentr. , 1954
98.
Alkyl- und Arylsulfens�ureanilide durch Cycloelimierung von Propen aus N-Aryl-S-isopropyl-sulfimiden
Claus P.K., Silbernagel W., Franek W., Rieder W.
Monatshefte fur Chemie , 1985
99.
101
M. F. Shostakovskii
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
100.
Syntheses and properties of novel cyclic sulfilimines, 2-azathiabenzene derivatives.
SHIMIZU H., MATSUO K., KATAOKA T., HORI M.
Chemical and Pharmaceutical Bulletin , 2011
101.
Synthesis of 1H-1,2,4-triazole 2-oxides and annelated derivatives
Gilchrist T.L., Harris C.J., Hawkins D.G., Moody C.J., Rees C.W.
Journal of the Chemical Society Perkin Transactions 1 , 1976
102.
Azasulfonium salts. Intermediates in a general procedure for the alkylation of aromatic amines
Gassman P.G., Gruetzmacher G.D.
Journal of the American Chemical Society , 1974
103.
Ring Expansion Reactions of 1,3-Dithiolanes to Dihydro-1,4-dithiines
YOSHINO H., KAWAZOE Y., TAGUCHI T.
Synthesis , 1974
104.
OrganicN-Halogen Compounds. X. Preparative Studies onN-Benzimidoylsulfilimines
Fuchigami T., Odo K.
Bulletin of the Chemical Society of Japan , 1977
105.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. , 1961
107.
Isolable Oxysulfuranes in Organic Chemistry
Martin J.C., Perozzi E.F.
Science , 1976
108.
110
M. F. Shostakovskii
Dokl. Akad. Nauk SSSR , 1960
110.
112
A. G. Pozdeeva
Zhur. Prikl. Khim. , 1952
111.
Stereoselective syntheses of substituted .gamma.-lactams from 3-alkenamides
Marson C.M., Grabowska U., Walsgrove T., Eggleston D.S., Baures P.W.
Journal of Organic Chemistry , 1991
112.
Synthesis, stereochemistry, and rearrangement of 9-alkylthioxanthene-N-(p-toluenesulfonyl)sulfilimines
Tamura Y., Nishikawa Y., Mukai C., Sumoto K., Ikeda M., Kise M.
Journal of Organic Chemistry , 1979
114.
116
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
115.
117
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
116.
118
V. M. Rodionov
Zhur. Obshch. Khim. , 1935
117.
119
V. V. Levchenko
Zhur. Obshch. Khim. , 1947
118.
120
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
119.
Chloramine T and related N-halogeno-N-metallo reagents
Campbell M.M., Johnson G.
Chemical Reviews , 1978
120.
122
S. R. Rafikov
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
121.
123
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
124.
126
J. Wiemannand Ch. Clachet
Compt. rend. , 1948
125.
Formation of triaminosulphonium and alkoxydiaminosulphonium ions
Minato H., Okuma K., Kobayashi M.
Journal of the Chemical Society Chemical Communications , 1975
126.
Sulfilimine and Sulfoximine VI The reaction of N-sulfonylsulfilimine with sulfoxide
Tsujihara K., Aida T., Furukawa N., Oae S.
Tetrahedron Letters , 1970
127.
129
J. Wiemann
Bull. Soc. chim. France , 1955
128.
The Michael Type Addition of Free Sulfilimine
FURUKAWA N., OAE S., YOSHIMURA T.
Synthesis , 1976
129.
ON THE REARRANGEMENT OFN-ARYL SULFIMIDES
Claus P.K., Schwarz H.A., Rieder W., Vycudilik W.
Phosphorous and Sulfur and the Related Elements , 1976
130.
Vilsmaier E., Huber M., Schütz J.
1980
131.
Isocyanatosulfonium‐Salze
Erhart M., Mews R., Pauer F., Stalke D., Sheldrick G.M.
Chemische Berichte , 1991
132.
134
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1948
133.
135
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1945
134.
136
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1954
135.
Specific o-alkylation of aromatic amines
Gassman P.G., Gruetzmacher G.
Journal of the American Chemical Society , 1973
137.
139
I. L. Knunyants
1959
139.
141
Friedl.
140.
142
1913
141.
143
Friedl.
142.
144
1912
143.
Selective ortho-alkylation of phenols with sulphoxides via[2,3]sigmatropic rearrangement: synthesis of coumarins
Sato K., Inoue S., Ozawa K., Kobayashi T., Ota T., Tazaki M.
Journal of the Chemical Society Perkin Transactions 1 , 1987
144.
146
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1952
145.
147
Y. Sasada
Acta Cryst. , 1898
146.
148
P. Kresse
Chem. Abs. , 1960
147.
149
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1954
148.
150
Ya. E. Bernadskaya
"Iskusstvennoe Volokno" (Artificial Fibres) , 1952
152.
154
Friedl.
153.
156
J. S. Fruton
J. Biol. Med. , 1950
155.
十字路
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry , 1989
157.
160
1912
158.
Reaction of Olefins with Dimethyl(methylthio)sulfonium Salts in the Presence of Triphenylphosphine. Preparation of Vinylphosphonium Salts
Okuma K., Koike T., Yamamoto S., Takeuchi H., Yonekura K., Ono M., Ohta H.
Bulletin of the Chemical Society of Japan , 1992
159.
Alkylthiolation of alkenes a novel synthesis of episulphonium ions (thiiranium ions)
Capozzi G., De Lucchi O., Lucchini V., Modena G.
Tetrahedron Letters , 1975
160.
S-Alkylthiolation of Sulphides. A Novel Synthesis of Alkylthiosulphonium Salts
CAPOZZI G., DELUCCHI O., LUCCHINI V., MODENA G.
Synthesis , 1976
161.
164
1917
162.
Aryl-bis(thioaryl)sulfonium salts and their use for the preparation of S-aryl-episulfonium salts
Gybin A.S., Smit W.A., Bogdanov V.S., Krimer M.Z., Kalyan J.B.
Tetrahedron Letters , 1980
163.
166
1917
165.
168
1918
166.
Chemistry of alkyl thiosulfinate esters. VI. Preparation and spectral studies
Block E., O'Connor J.
Journal of the American Chemical Society , 1974
167.
170
1918
168.
Thioammonium ions. Azasulfenylation reactions
Caserio M.C., Kim J.K.
Journal of the American Chemical Society , 1982
169.
172
1918
173.
Methylthiolation of allylic sulfides. A degenerate [2,3]-sigmatropic rearrangement
Kim J.K., Kline M.L., Caserio M.C.
Journal of the American Chemical Society , 1978
174.
1H and 13C nuclear magnetic resonance evidence for a long-lived thiirenium ion
Capozzi G., De Lucchi O., Lucchini V., Modena G.
Journal of the Chemical Society Chemical Communications , 1975
175.
178
1946
176.
Oxosulfonium Salts. III. Methylation of Optically Active Sulfoxides.
Kamiyama K., Minato H., Kobayashi M.
Bulletin of the Chemical Society of Japan , 1973
177.
An aldehyde synthesis utilizing the thiazole ring system.
Altman L.J., Richheimer S.L.
Tetrahedron Letters , 1971
178.
Neighboring Group Participation in the Halogenation of Sulfoxides
Durst T., Tin K.-., Marcil M.J.
Canadian Journal of Chemistry , 1973