Home / Articles / Synthesis and properties of sultines, cyclic esters of sulfinic acids

Synthesis and properties of sultines, cyclic esters of sulfinic acids

Oxana Borisovna Bondarenko 1
Oxana Borisovna Bondarenko
, 
Lyudmila Galievna Saginova 1
Lyudmila Galievna Saginova
, 
Nikolai Vasil'evich Zyk 1
Nikolai Vasil'evich Zyk
1 M. V. Lomonosov Moscow State University, Department of Chemistry
Published 30 November 1995
Communication , Volume 65, Issue 2, 147-166
28
Share
Cite this
GOST
 | 
Cite this
GOST
Bondarenko O. B., Saginova L. G., Zyk N. V. Synthesis and properties of sultines, cyclic esters of sulfinic acids // Russian Chemical Reviews. 1996. Vol. 65. No. 2. pp. 147-166.
GOST all authors (up to 50)
Bondarenko O. B., Saginova L. G., Zyk N. V. Synthesis and properties of sultines, cyclic esters of sulfinic acids // Russian Chemical Reviews. 1996. Vol. 65. No. 2. pp. 147-166.
RIS
 | 
Cite this
RIS
TY - JOUR
DO - 10.1070/RC1996v065n02ABEH000204
UR - https://rcr.colab.ws/publications/10.1070/RC1996v065n02ABEH000204
TI - Synthesis and properties of sultines, cyclic esters of sulfinic acids
T2 - Russian Chemical Reviews
AU - Bondarenko, Oxana Borisovna
AU - Saginova, Lyudmila Galievna
AU - Zyk, Nikolai Vasil'evich
PY - 1996
DA - 1995/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 147-166
IS - 2
VL - 65
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
@article{1996_Bondarenko,
author = {Oxana Borisovna Bondarenko and Lyudmila Galievna Saginova and Nikolai Vasil'evich Zyk},
title = {Synthesis and properties of sultines, cyclic esters of sulfinic acids},
journal = {Russian Chemical Reviews},
year = {1996},
volume = {65},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1996v065n02ABEH000204},
number = {2},
pages = {147--166},
doi = {10.1070/RC1996v065n02ABEH000204}
}
MLA
Cite this
MLA
Bondarenko, Oxana Borisovna, et al. “Synthesis and properties of sultines, cyclic esters of sulfinic acids.” Russian Chemical Reviews, vol. 65, no. 2, Nov. 1996, pp. 147-166. https://rcr.colab.ws/publications/10.1070/RC1996v065n02ABEH000204.
Views / Visits / Downloads
13 / 13 / 3

Abstract

Data on the synthesis and chemical properties of sultines, cyclic esters of sulfinic acids, are reviewed. The known methods for synthesising sultines are considered, the reaction mechanisms and stereochemistry of the compounds obtained are discussed. The chemical transformations of sultines, including photolysis, thermolysis, redox reactions, and interaction with nucleophiles, are described. The bibliography includes 109 references.

References

1.
Ueber verseifbare Sulfone, Sulfonsulfinsäuren und Sulfinsäurelactone
Baumann E., Walter G.
Berichte der deutschen chemischen Gesellschaft , 1893
3.
Thermal and Ionic Cyclizations of Allenic Sulfones and Sulfinates
Braverman S.
Phosphorous and Sulfur and the Related Elements , 1985
4.
4
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
5.
Cyclic sulphinic acid derivatives (sultines and sulphinamides)
Dittmer D.C., Hoey M.D.
Chemistry of Functional Groups , 1990
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
9.
Thermolysis of thiete 1,1-dioxide and related species
King J.F., Mayo P.D., McIntosh C.L., Piers K., Smith D.J.
Canadian Journal of Chemistry , 1970
10.
Chlorination of Heterocyclic and Acyclic Sulfonhydrazones
King J.F., Hawson A., Huston B.L., Danks L.J., Komery J.
Canadian Journal of Chemistry , 1971
11.
Synthesis and Thermolysis of 2H-1,2,3-Benzothiadiazine 1,1-Dioxide and 2,1-Benzoxathiin-3-one 1,1-Dioxide
King J.F., Huston B.L., Hawson A., Komery J., Deaken D.M., Harding D.R.
Canadian Journal of Chemistry , 1971
13.
Thietanes. IV. Rearrangement of 2,4-diphenylthietane oxides
Dodson R.M., Hammen P.D., Fan J.Y.
Journal of Organic Chemistry , 1971
14.
14
V. B. Evstigneev
Zhur. Fiz. Khim. , 1958
15.
15
A. S. Holt
"Research in Photosynthesis" , 1957
19.
19
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1959
20.
Cyclic sulfinate ester. Preparation and reactions of 1,2-benzoxathiane 2-oxide
Givens E.N., Hamilton L.A.
Journal of Organic Chemistry , 1967
21.
Synthesis and ring-opening reactions of functionalized sultines. New approach to sparsomycin
Liskamp R.M., Zeegers H.J., Ottenheijm H.C.
Journal of Organic Chemistry , 1981
23.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR , 1958
24.
3,3,4,4-Tetraphenyl-1,2-oxathiolan-5-one 2-oxide. Synthesis, structure, and selected chemistry
Kohn H., Charumilind P., Simonsen S.H.
Journal of the American Chemical Society , 1979
26.
Decomposition of 3,6-dihydro-1,2-oxathiin 2-oxides to sulfur dioxide and 1,3-dienes. A .pi.4s+.pi.2s cycloreversion
Jung F., Molin M., Van der Elzen R., Durst T.
Journal of the American Chemical Society , 1974
27.
Synthesis of sultines via tert-butyl hydroxyalkyl sulfoxides
Sharma N.K., Reinach-Hirtzbach F.D., Durst T.
Canadian Journal of Chemistry , 1976
28.
Synthesis and X-ray crystal structure determination of 3,4-diphenyl-6-(diphenylmethyl)-1,5-dioxa-2-thiane-2-oxide
29.
A novel stereoselective route to γ-butyrolactones
Casey M., Manage A.C., Murphy P.J.
Tetrahedron Letters , 1992
30.
Neighboring Group Participation in the Halogenation of Sulfoxides
Durst T., Tin K.-., Marcil M.J.
Canadian Journal of Chemistry , 1973
31.
Reactions of β-hydroxy sulfoxides with N-bromosuccinimide
Taguchi H., Yamamoto H., Nozaki H.
Tetrahedron Letters , 1973
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.
Isoprene functionalization
Nederlof P.J., Moolenaar M.J., de Waard E.R., Huisman H.O.
Tetrahedron , 1978
35.
Cyclic Alkoxyoxosulfonium Ions in the Chlorination of Hydroxy Sulfoxides
Durst T., Tin K.-.
Canadian Journal of Chemistry , 1971
36.
Conformational analysis of substituted 1,2-oxathiane 2-oxides by 13C and 1H nuclear magnetic resonance spectroscopy
Buchanan G.W., Sharma N.K., Reinach-Hirtzbach F.D., Durst T.
Canadian Journal of Chemistry , 1977
37.
Conformational analysis of sulfur-containing heterocycles. Dipolar effect
Harpp D.N., Gleason J.G.
Journal of Organic Chemistry , 1971
38.
Dipole Moments and Conformation of Sultones, Thiosultones, and Sultines
Exner O., Harpp D.N., Gleason J.G.
Canadian Journal of Chemistry , 1972
39.
.beta.-Sultines. Intermediates in a sulfur analog of the Wittig olefin synthesis
Jung F., Sharma N.K., Durst T.
Journal of the American Chemical Society , 1973
41.
Isolation and characterization of a stable 1,2-oxathietan 2-oxide (β-sultine)
Durst T., Gimbarzevsky B.P.
Journal of the Chemical Society Chemical Communications , 1975
44.
Reactions of 1-hydroxy-1,3-dihydrobenzo[c]thiophen-2,2-dioxides. Preparation of benz-fused δ-sultines
45.
494. Tracer studies in ester hydrolysis. Part X. The hydrolysis of methyl toluene-p-sulphinate
Bunton C.A., Hendy B.N.
Journal of the Chemical Society (Resumed) , 1962
48.
Eine einfache Synthese von γ-Sultinen
Messinger P.
Archiv der Pharmazie , 1985
49.
Preparation, characterization, and flash vacuum pyrolysis of dibenz[c,e][1,2]oxathiin 6-oxide (biphenylene sultine)
Squires T.G., Venier C.G., Hodgson B.A., Chang L.W., Davis F.A., Panunto T.W.
Journal of Organic Chemistry , 1981
50.
50
G. Glacomello
Gazzetta. , 1935
51.
51
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
52.
Organic sulfur chemistry. 26. Synthesis and reactions of some new sulfur transfer reagents
Harpp D.N., Steliou K., Chan T.H.
Journal of the American Chemical Society , 1978
53.
Organic Esters of Bivalent Sulfur. III. Sulfoxylates
Thompson Q.E.
Journal of Organic Chemistry , 1965
54.
The Reactions of Sodium 1-Benzyl-1,4-dihydronicotinamide-4-sulfinate with Halogen Compounds
Inoue H., Inoguchi N., Imoto E.
Bulletin of the Chemical Society of Japan , 1977
55.
55
G. A. Bogdanovskii
1958
56.
The reaction of thionyl chloride with some Tricyclo[3,2,1,02,4]oct-6-en-8-ols
Henrick K., Johnson B.
Australian Journal of Chemistry , 1972
57.
Stereocontrolled syntheses of novel cyclic sulfinates using N-sulfinyl-p-toiuenesulfonamide
Marson C.M., Giles P.R., Adams H., Bailey N.A.
Journal of the Chemical Society Chemical Communications , 1993
60.
The Interaction of Sulfur Dioxide with Aromatic Substances
Andrews L.J., Keefer R.M.
Journal of the American Chemical Society , 1951
62.
62
A. A. Krasnovskii
"Sbornik, Voprosy Khimicheskoi Kinetiki" (Symposium, Problems of Chemical Kinetics) , 1955
64.
Thermodynamics of formation and absorption spectra of 1:1 complexes between sulphur dioxide and olefines
66.
The geometry of the charge transfer complex (CH3)3N,SO2 in the solid state
van der Helm D., Childs J.D., Christian S.D.
Journal of the Chemical Society D Chemical Communications , 1969
67.
67
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1940
70.
SbF5-catalysed addition of SO2 to hexamethyldewarbenzene
Hogeveen H., Jorritsma H., Kwant P.W.
Tetrahedron Letters , 1975
71.
9-Thiabicyclo[4.2.1]nona-2,4,7-triene 9,9-dioxide
Gasteiger J., Huisgen R.
Journal of the American Chemical Society , 1972
72.
Direct 1,5-cycloaddition of sulphur dioxide to cyclo-octatetraene. 9-Thiabarbaralane 9,9-dioxide
Paquette L.A., Jacobsson U., Oku M.
Journal of the Chemical Society Chemical Communications , 1975
74.
Crystal and molecular structure of the 1:1 adduct of antimony(V) fluoride and sulfur dioxide
Moore J.W., Baird H.W., Miller H.B.
Journal of the American Chemical Society , 1968
76.
Onium ions. 21. Cyclopropylhalonium ions
Olah G.A., Prakash G.K., Bruce M.R.
Journal of the American Chemical Society , 1979
77.
77
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
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.
Photochemical addition of sulfur dioxide to certain arylcyclopropanes
Applequist D.E., McKenzie L.F.
Journal of Organic Chemistry , 1977
84.
Reaction of a benzvalene with sulfur dioxide. A chemical cascade
Hogeveen H., Zwart L.
Journal of the American Chemical Society , 1982
85.
The Photoreversible Addition of Sulfur Dioxide to Benzobenzvalene: A new Approach to the Benzoprefulvene Biradical
86.
Cationic metal-carbene complexes in cycloaddition reactions. Synthesis and reactions of iron-cyclopropyl complexes
Cutler A., Fish R.W., Giering W.P., Rosenblum M.
Journal of the American Chemical Society , 1972
87.
Sulfur doxide insertion. XV. Transition metal-vinyl complexes containing a sultine ring
Thomasson J.E., Robinson P.W., Ross D.A., Wojcicki A.
Inorganic Chemistry , 1971
89.
An electrosynthesis of sulphones
Knittel D., Kastening B.
Journal of Applied Electrochemistry , 1973
90.
An e.s.r. investigation of the complex formation between SO2 and electrogenerated SO2−.
Kastening B., Gostiša-Mihelčić B.
Journal of Electroanalytical Chemistry and Interfacial Electrochemistry , 1979
93.
Pyrolysis and Mass Spectrum of Dibenzothiophene 5,5-Dioxide
Fields E.K., Meyerson S.
Journal of the American Chemical Society , 1966
94.
The flash thermolysis of γ-sultines
Durst T., Finlay J.D., Smith D.J.
Journal of the Chemical Society Perkin Transactions 1 , 1979
95.
Photochemical extrusion of sulfur dioxide from sultines
Durst T., Huang J.C., Sharma N.K., Smith D.J.
Canadian Journal of Chemistry , 1978
96.
Thermolysis of the sulfur dioxide adducts of benzobenzvalene. The 1.3-dipolar behaviour of a sulfene
Burger U., Erne-Zellweger D., Sledeski A.W., Schmidlin S.
Tetrahedron Letters , 1989
97.
Flash vacuum thermolysis of functionalized .gamma.-sultines
Liskamp R.M., Blom H.J., Nivard R.J., Ottenheijm H.C.
Journal of Organic Chemistry , 1983
98.
Sultone chemistry
Roberts D.W., Williams D.L.
Tetrahedron , 1987
99.
Lithium aluminum hydride reduction of terpene sultones
Wolinsky J., Marhenke R.L.
Journal of Organic Chemistry , 1975
100.
Reductive formation of disulfides from sulfenyl, sulfinyl, and sulfonyl derivatives using tri-n-propylamine and trichlorosilane
Chan T., Montillier J.P., Van Horn W.F., Harpp D.N.
Journal of the American Chemical Society , 1970
101.
Ring opening and closure and oxygen isotope exchange of cyclic sulfinate esters
Okuyama T., Takano H., Ohnishi K., Nagase S.
Journal of Organic Chemistry , 1994
102.
102
F. Fichter
Helv. Chim. Acta , 1922
103.
103
L. N. Bell
Dokl. Akad. Nauk SSSR , 1956
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.
Mechanism and Reactivity of Hydrolysis of Aliphatic Sulfonate Esters
Mori A., Nagayama M., Mandai H.
Bulletin of the Chemical Society of Japan , 1971
108.
The Chemistry of Sultones and Sultams.
Mustafa A.
Chemical Reviews , 1954
109.
Nucleophilic substitution at sulphur. Part 3. The alkaline hydrolysis of some cyclic and open-chain sulphonate esters
Laleh A., Ranson R., Tillett J.G.
Journal of the Chemical Society Perkin Transactions 2 , 1980
111.
111
M. Calvin
1956