Home / Articles / Methods for the synthesis of O-, S- and N-vinyl derivatives

Methods for the synthesis of O-, S- and N-vinyl derivatives

Maria Sergeevna Ledovskaya 1
Maria Sergeevna Ledovskaya
, 
Vladimir Vladimirovich Voronin
, 
Konstantin Sergeevich Rodygin 1
Konstantin Sergeevich Rodygin
1 Saint Petersburg State University
Published 30 November 2017
51
Share
Cite this
GOST
 | 
Cite this
GOST
Ledovskaya M. S., Voronin V. V., Rodygin K. S. Methods for the synthesis of O-, S- and N-vinyl derivatives // Russian Chemical Reviews. 2017. Vol. 87. No. 2. pp. 167-191.
GOST all authors (up to 50)
Ledovskaya M. S., Voronin V. V., Rodygin K. S. Methods for the synthesis of O-, S- and N-vinyl derivatives // Russian Chemical Reviews. 2017. Vol. 87. No. 2. pp. 167-191.
RIS
 | 
Cite this
RIS
TY - JOUR
DO - 10.1070/RCR4782
UR - https://rcr.colab.ws/publications/10.1070/RCR4782
TI - Methods for the synthesis of O-, S- and N-vinyl derivatives
T2 - Russian Chemical Reviews
AU - Ledovskaya, Maria Sergeevna
AU - Voronin, Vladimir Vladimirovich
AU - Rodygin, Konstantin Sergeevich
PY - 2017
DA - 2017/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 167-191
IS - 2
VL - 87
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
@article{2017_Ledovskaya,
author = {Maria Sergeevna Ledovskaya and Vladimir Vladimirovich Voronin and Konstantin Sergeevich Rodygin},
title = {Methods for the synthesis of O-, S- and N-vinyl derivatives},
journal = {Russian Chemical Reviews},
year = {2017},
volume = {87},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4782},
number = {2},
pages = {167--191},
doi = {10.1070/RCR4782}
}
MLA
Cite this
MLA
Ledovskaya, Maria Sergeevna, et al. “Methods for the synthesis of O-, S- and N-vinyl derivatives.” Russian Chemical Reviews, vol. 87, no. 2, Nov. 2017, pp. 167-191. https://rcr.colab.ws/publications/10.1070/RCR4782.
Views / Visits / Downloads
31 / 30 / 48

Abstract

The currently known methods for the preparation of vinyl ethers, vinyl sulfides and enamines are analyzed and described systematically. The published data on the reactions of alcohols, thiols and various nitrogen-containing compounds with acetylene, resulting in the corresponding vinyl derivatives, are considered. The attention is focused on the application of convenient acetylene sources. Other modern approaches to the synthesis of vinyl derivatives are described in detail, including vinyl exchange and metathesis reactions, various types of cross-coupling and cleavage of organic compounds. Some specific synthetic routes to vinyl ethers, vinyl sulfides and enamines are presented in the last Section.

The bibliography includes 262 references.

Funders

Russian Science Foundation
16-13-10301

References

1.
rcr_87_2_167bib1
Tedeschi
1982
2.
Vinyl Ether/Tetrazine Pair for the Traceless Release of Alcohols in Cells
Jiménez-Moreno E., Guo Z., Oliveira B.L., Albuquerque I.S., Kitowski A., Guerreiro A., Boutureira O., Rodrigues T., Jiménez-Osés G., Bernardes G.J.
Angewandte Chemie - International Edition , 2016
3.
Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates
Wallbaum J., Garve L.K., Jones P.G., Werz D.B.
Organic Letters , 2016
6.
Ring-Opening 1,3-Dichlorination of Donor–Acceptor Cyclopropanes by Iodobenzene Dichloride
Garve L.K., Barkawitz P., Jones P.G., Werz D.B.
Organic Letters , 2014
7.
Donor-Substituted Nitrocyclopropanes: Immediate Ring-Enlargement to Cyclic Nitronates
Schmidt C.D., Kaschel J., Schneider T.F., Kratzert D., Stalke D., Werz D.B.
Organic Letters , 2013
8.
Synthesis of (+)-7,20-Diisocyanoadociane and Liver-Stage Antiplasmodial Activity of the Isocyanoterpene Class
Lu H., Pronin S.V., Antonova-Koch Y., Meister S., Winzeler E.A., Shenvi R.A.
Journal of the American Chemical Society , 2016
12.
Broadly ApplicableZ- and Diastereoselective Ring-Opening/Cross-Metathesis Catalyzed by a Dithiolate Ru Complex
Koh M.J., Khan R.K., Torker S., Hoveyda A.H.
Angewandte Chemie - International Edition , 2014
13.
rcr_87_2_167bib13
Khan
J. Am. Chem. Soc. , 2012
14.
Intermolecular Enol Ether−Alkyne Metathesis
Giessert A.J., Snyder L., Markham J., Diver S.T.
Organic Letters , 2003
15.
Coupling Reaction of Enol Derivatives with Silyl Ketene Acetals Catalyzed by Gallium Trihalides
Nishimoto Y., Kita Y., Ueda H., Imaoka H., Chiba K., Yasuda M., Baba A.
Chemistry - A European Journal , 2016
16.
Diarylrhodates as Promising Active Catalysts for the Arylation of Vinyl Ethers with Grignard Reagents
Iwasaki T., Miyata Y., Akimoto R., Fujii Y., Kuniyasu H., Kambe N.
Journal of the American Chemical Society , 2014
17.
ADDITION OF ALCOHOLS AND MERCAPTANS TO COMPOUNDS WITH TRIPLE BONDS
Shostakovskii M.F., Bogdanova A.V., Plotnikova G.I.
Russian Chemical Reviews , 1964
18.
rcr_87_2_167bib18
Favorskii
Zh. Obshch. Khim. , 1943
19.
rcr_87_2_167bib19
Shostakovskii
1952
20.
Synthesis of Vinyl Ethers Containing Functional Groups and Heteroatoms
Shostakovskii M.F., Trofimov B.A., Atavin A.S., Lavrov V.I.
Russian Chemical Reviews , 1968
21.
Catalytic reactions of acetylene: a feedstock for the chemical industry revisited.
22.
rcr_87_2_167bib22
1933
23.
Reactions of acetylenes in superbasic media. Recent advances
Trofimov B.A., Schmidt E.Y.
Russian Chemical Reviews , 2014
24.
rcr_87_2_167bib24
Ananikov
2013
25.
rcr_87_2_167bib25
Ananikov
2013
26.
Vinylation Rates of Primary, Secondary, and Tertiary Alcohols
27.
rcr_87_2_167bib27
Shostakovskii
Izv. Akad. Nauk USSR, Ser. Khim. , 1957
28.
Vinylation: Kinetics and Mechanism of the Methoxide-catalyzed Addition of Methanol to Phenylacetylene1
29.
Vinylation. II.1 Stereochemistry and Synthesis of β-Methoxystyrenes2
Miller S.I.
Journal of the American Chemical Society , 1956
30.
rcr_87_2_167bib30
Ban
J. Chem. Soc. Jpn., Pure Chem. Sect. , 1956
32.
rcr_87_2_167bib32
Trofimov
1981
33.
2-Phenylpyrrole: one-pot selective synthesis from acetophenone oxime and acetylene by a Trofimov reaction*
Mikhaleva A.I., Petrova O.V., Sobenina L.N.
Chemistry of Heterocyclic Compounds , 2012
34.
rcr_87_2_167bib34
Trofimov
Russ. J. Org. Chem. , 1995
35.
Nucleophilic Addition to Acetylenes in Superbasic Catalytic Systems: X. Catalytic Effect of Alkali Metal Hydroxides in the Vinylation of 1-Heptanol
Parshina L.N., Oparina L.A., Gorelova O.V., Preiss T., Henkelmann J., Trofimov B.A.
Russian Journal of Organic Chemistry , 2001
36.
Nucleophilic addition to acetylenes in superbasic catalytic systems: XVIII. Vinylation of phenols and naphthols with acetylene
Trofimov B.A., Oparina L.A., Kolyvanov N.A., Vysotskaya O.V., Gusarova N.K.
Russian Journal of Organic Chemistry , 2015
37.
Exploring acetylene chemistry in superbasic media: A theoretical study of the effect of water on vinylation and ethynylation reactions with acetylene in KOH/DMSO and NaOH/DMSO systems
Vitkovskaya N.M., Orel V.B., Kobychev V.B., Bobkov A.S., Larionova E.Y., Trofimov B.A.
Journal of Physical Organic Chemistry , 2016
38.
Nucleophilic Addition to Acetylenes in Superbasic Catalytic Systems: XI. Transformations of Alkali Metal Hydroxides during Vinylation of 1-Heptanol with Acetylene under Elevated Pressure
Oparina L.A., Parshina L.N., Khil'ko M.Y., Gorelova O.V., Preiss T., Henkelmann J., Trofimov B.A.
Russian Journal of Organic Chemistry , 2001
39.
Nucleophilic Addition to Acetylenes in Superbasic Catalytic Systems: XIII. Fluoride Cesium Containing Systems, Efficient Catalysts for Alkanols Vinylation
Oparina L.A., Shaikhudinova S.I., Parshina L.N., Vysotskaya O.V., Preiss T., Henkelmann J., Trofimov B.A.
Russian Journal of Organic Chemistry , 2005
40.
rcr_87_2_167bib40
Trofimov
Zh. Org. Khim. , 1990
43.
Nucleophilic addition to acetylenes in superbasic catalytic systems: XVI. Vinylation of alcohols of the furan series under atmospheric pressure
Oparina L.A., Vysotskaya O.V., Stepanov A.V., Gusarova N.K., Trofimov B.A.
Russian Journal of Organic Chemistry , 2009
44.
Direct vinylation of glucose derivatives with acetylene
Trofimov B.A., Parshina L.N., Oparina L.A., Tantsyrev A.P., Khil'ko M., Vysotskaya O.V., Stepanov A.V., Gusarova N.K., Henkelmann J.
Tetrahedron , 2007
45.
Structural study of 2,3,4,6-tetra(O-vinyl) methyl-α-d-glucopyranoside
Trofimov B.A., Oparina L.A., Krivdin L.B., Gusarova N.K., Chernyshev K.A., Sinegovskaya L.M., Klyba L.V., Parshina L.N., Tantsyrev A.P., Kazheva O.N., Alexandrov G.G., D'yachenko O.A.
Journal of Molecular Structure , 2006
46.
Vinylation of cellulose in superbase catalytic systems: towards new biodegradable polymer materials
Trofimov B.A., Oparina L.A., Parshina L.N., Khil’ko M.Y., Tantsyrev A.P., Aleksandrova G.P.
Cellulose , 2013
48.
rcr_87_2_167bib48
2001
49.
Trofimov Boris Aleksandrovich, Schmidt Elena Yur'evna, Skital’tseva Elena V, Bidusenko Ivan A., Zorina Nadezhda Victorovna, Mikhaleva Albina Ivanovna
Mendeleev Communications , 2012
51.
Carboxylic Group-Assisted Proton Transfer in Gold-Mediated Thiolation of Alkynes
Zalesskiy S.S., Khrustalev V.N., Kostukovich A.Y., Ananikov V.P.
Organometallics , 2015
52.
Catalytic adaptive recognition of thiol (SH) and selenol (SeH) groups toward synthesis of functionalized vinyl monomers
Ananikov V.P., Orlov N.V., Zalesskiy S.S., Beletskaya I.P., Khrustalev V.N., Morokuma K., Musaev D.G.
Journal of the American Chemical Society , 2012
53.
Pd-NHC Catalytic System for the Efficient Atom-Economic Synthesis of Vinyl Sulfides from Tertiary, Secondary, or Primary Thiols
Degtyareva E.S., Burykina J.V., Fakhrutdinov A.N., Gordeev E.G., Khrustalev V.N., Ananikov V.P.
ACS Catalysis , 2015
55.
Catalyst leaching as an efficient tool for constructing new catalytic reactions: application to the synthesis of cyclic vinyl sulfides and vinyl selenides
Ananikov V.P., Gayduk K.A., Beletskaya I.P., Khrustalev V.N., Antipin M.Y.
European Journal of Inorganic Chemistry , 2009
56.
rcr_87_2_167bib56
Shostakovskii
Izv. Akad. Nauk SSSR. Ser. Khim. , 1954
57.
rcr_87_2_167bib57
Prilezhaeva
Izv. Akad. Nauk SSSR. Ser. Khim. , 1954
58.
rcr_87_2_167bib58
Shostakovskii
Izv. Akad. Nauk SSSR. Ser. Khim. , 1955
59.
rcr_87_2_167bib59
2006
60.
Highly efficient atom economical “green chemistry” synthesis of vinyl sulfides from thiols and acetylene in water
Gusarova N.K., Chernysheva N.A., Yas’ko S.V., Trofimov B.A.
Russian Chemical Bulletin , 2013
61.
Vinyl Sulfides. I. A “One-Step” Synthesis from Halides
SCHNEIDER H.J., BAGNELL J.J., MURDOCH G.C.
Journal of Organic Chemistry , 1961
62.
Vinyl Sulfides. II. Aminoalkyl Vinyl Sulfides
SCHNEIDER H.J., BAGNELL J.J., MURDOCH G.C.
Journal of Organic Chemistry , 1961
63.
rcr_87_2_167bib63
Bhattacharya
2008
64.
Divinyl Sulfide: Synthesis, Properties, and Applications
67.
rcr_87_2_167bib67
Bühler
2005
68.
rcr_87_2_167bib68
1936
69.
rcr_87_2_167bib69
Domnina
Chem. Heterocycl. Compd. , 1966
70.
Improved method for the synthesis of 1-vinylindole
Shmidt E.Y., Protsuk N.I., Vasil’tsov A.M., Ivanov A.V., Mikhaleva A.I., Trofimov B.A.
Chemistry of Heterocyclic Compounds , 2013
71.
rcr_87_2_167bib71
1943
72.
Synthesis and characterization of different poly(1-vinylindole)s for photorefractive materials
Brustolin F., Castelvetro V., Ciardelli F., Ruggeri G., Colligiani A.
Journal of Polymer Science, Part A: Polymer Chemistry , 2000
73.
rcr_87_2_167bib73
Lin
J. Polym. Sci.: Polym. Chem. Ed. , 1979
74.
rcr_87_2_167bib74
Stepanova
Khim. Geterotsikl. Soedin. , 1986
75.
Calcium Carbide: A Unique Reagent for Organic Synthesis and Nanotechnology
Rodygin K.S., Werner G., Kucherov F.A., Ananikov V.P.
Chemistry - An Asian Journal , 2016
76.
Direct vinylation of natural alcohols and derivatives with calcium carbide
Teong S.P., Chua A.Y., Deng S., Li X., Zhang Y.
Green Chemistry , 2017
77.
A solid acetylene reagent with enhanced reactivity: fluoride-mediated functionalization of alcohols and phenols
Werner G., Rodygin K.S., Kostin A.A., Gordeev E.G., Kashin A.S., Ananikov V.P.
Green Chemistry , 2017
78.
An Atom‐Economic Approach for Vinylation of Indoles and Phenols Using Calcium Carbide as Acetylene Surrogate
Rattanangkool E., Vilaivan T., Sukwattanasinitt M., Wacharasindhu S.
European Journal of Organic Chemistry , 2016
80.
Rodygin Konstantin Sergeevich, Kostin Anton Alekseevich, Ananikov Valentin Pavlovich
Mendeleev Communications , 2015
82.
rcr_87_2_167bib82
1937
89.
rcr_87_2_167bib89
Gareev
Zh. Org. Khim. , 1975
90.
Development of a highly efficient catalytic method for synthesis of vinyl ethers.
Okimoto Y., Sakaguchi S., Ishii Y.
Journal of the American Chemical Society , 2002
91.
The palladium (II) catalyzed vinyl interchange reaction—I
McKeon J.E., Fitton P., Griswold A.A.
Tetrahedron , 1972
98.
Synthesis of Dihydroisoxazole Nucleoside and Nucleotide Analogs
Gi H., Xiang Y., Schinazi R.F., Zhao K.
Journal of Organic Chemistry , 1997
99.
rcr_87_2_167bib99
Dalpozzo
Synthesis , 2002
100.
9-Vinylguanine: an easy access to aza-analogs of 2′,3′-dideoxyguanosine
Dalpozzo R., De Nino A., Maiuolo L., Procopio A., De Munno G., Sindona G.
Tetrahedron , 2001
103.
Synthesis of N-Vinyl-1,2,3-triazole Derivatives
Kizhnyaev V.N., Pokatilov F.A., Tsypina N.A., Ratovskii G.V., Vereshchagin L.I., Smirnov A.I.
Russian Journal of Organic Chemistry , 2002
104.
Iridium-Catalyzed Vinylation of Carbazole Derivatives with Vinyl Acetate
105.
Synthesis of [2,3,4,5-14C]-1-vinyl-2-pyrrolidinone
Digenis G.A., McClanahan J.S., Chen P.
Journal of Labelled Compounds and Radiopharmaceuticals , 1993
106.
Synthesis of P,N-Heterocycles from ω-Amino-H-Phosphinates: Conformationally Restricted α-Amino Acid Analogs
107.
The Cohalogenation of 1-N-Vinylpyrimidinediones: A New Approach to Nucleoside Analogs
Baret N., Dulcere J., Rodriguez J., Pons J., Faure R.
European Journal of Organic Chemistry , 2000
111.
rcr_87_2_167bib111
Pielichowski
J. Polym. Sci.: Polym. Lett. Ed. , 1976
112.
rcr_87_2_167bib112
Pielichowski
J. Polym. Sci.: Polym. Lett. Ed. , 1974
113.
rcr_87_2_167bib113
Dehmlov
1975
114.
rcr_87_2_167bib114
Weber
1977
115.
Synthesis of N- and S-Vinyl Derivatives of Heteroaromatic Compounds Using Phase-transfer Catalysis
Abele E., Dzenitis O., Rubina K., Lukevics E.
Chemistry of Heterocyclic Compounds , 2002
117.
rcr_87_2_167bib117
1982
118.
rcr_87_2_167bib118
1982
119.
rcr_87_2_167bib119
Pielichowski
J. Polym. Sci.: Polym. Lett. Ed. , 1985
121.
rcr_87_2_167bib121
Reno
Org. Synth. , 1998
122.
Vinyl sulfide hydrolysis
McClelland R.A.
Canadian Journal of Chemistry , 1977
124.
Azoles. Part 4. Nucleophilic substitution reactions of halogenoimidazoles
Iddon B., Khan N., Lim B.L.
Journal of the Chemical Society Perkin Transactions 1 , 1987
126.
STUDIES ON THE MICHAEL-TYPE REACTION OFS-VINYL SULFILIMINE
Yamamoto T., Okawara M.
Chemistry Letters , 1975
128.
Synthesis of N-Vinylpyrazoles
Attarian O.S., Matsoyan S.G., Martirosyan S.S.
Chemistry of Heterocyclic Compounds , 2005
129.
Dehydrochlorination of 1-(2-chloroethyl)azoles in aqueous solution of N-methylmorpholine N-oxide
Zakaryan G.B., Hayotsyan S.S., Attaryan H.S., Hasratyan G.V.
Russian Journal of General Chemistry , 2016
131.
Triisopropylsilanol: A new type of phase transfer catalyst for dehydrohalogenation
Soderquist J.A., Vaquer J., Diaz M.J., Rane A.M., Bordwell F.G., Zhang S.
Tetrahedron Letters , 1996
132.
N-Vinyl derivatives of substituted pyrimidines and purines
Pitha J., Ts'o P.O.
Journal of Organic Chemistry , 1968
134.
Nucleic acid analogs. The syntheses of poly-1-vinyluracil and poly-9-vinyladenine
135.
Competitive Elimination-Substitution Reactions. Some Dramatic Differences between Bromides and Tosylates
Veeravagu P., Arnold R.T., Eigenmann E.W.
Journal of the American Chemical Society , 1964
136.
Preparatory Method for N-Vinyl-2-pyrrolidone
Puetzer B., Katz L., Horwitz L.
Journal of the American Chemical Society , 1952
137.
Über die Bildung von Lactamen aus Lactonen
Späth E., Lintner J.
Berichte der deutschen chemischen Gesellschaft (A and B Series) , 1936
138.
Development of a New Production Process forN-Vinyl-2-pyrrolidone
Shimasaki Y., Yano H., Sugiura H., Kambe H.
Bulletin of the Chemical Society of Japan , 2008
139.
Development of a New Production Process for N-Vinyl-2-Pyrrolidone
Shimasaki Y., Yano H.
Catalysis Surveys from Asia , 2010
142.
THE SYNTHESIS OF ALPHA,BETA-UNSATURATED ETHERS
Lauer W.M., Spielman M.A.
Journal of the American Chemical Society , 1931
143.
The Thermal Decomposition of Phenyl Vinyl Ether
Lauer W.M., Spielman M.A.
Journal of the American Chemical Society , 1933
144.
Ketene Acetals. XV. Ketene Diphenylacetal and Triphenyl Orthoacetate
McElvain S.M., Fajardo-Pinzón B.
Journal of the American Chemical Society , 1945
146.
Hydroformylation of aryloxy ethylenes by Rh/BINAPHOS complex
Solinas M., Gladiali S., Marchetti M.
Journal of Molecular Catalysis A Chemical , 2005
148.
Copolymerization Characteristics and Spectra of Phenyl Vinyl Sulfide and Sulfone
Price C.C., Morita H.
Journal of the American Chemical Society , 1953
149.
Acid-catalyzed hydrolysis of ring-substituted phenyl vinyl sulfides
Okuyama T., Masago M., Nakada M., Fueno T.
Tetrahedron , 1977
150.
A Convenient Method for the Introduction of a Vinylthio Group
VERBOOM W., MEIJER J., BRANDSMA L.
Synthesis , 1978
152.
Preparation and Purification of 4-Nitrophenyl Vinyl Ether
DOMBROSKI J.R., HALLENSLEBEN M.L.
Synthesis , 1972
153.
rcr_87_2_167bib153
Wu
J. Am. Chem. Soc. , 2016
154.
Synthesis of malondialdehyde-1,2,3-14C3 via ethyl vinyl-[1,2-14C2] ether
Bienkowski M.J., Tuttle M.A., Marnett L.J.
Journal of Labelled Compounds and Radiopharmaceuticals , 1980
155.
Lipid peroxidation-DNA damage by malondialdehyde.
Marnett L.J.
Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis , 1999
156.
Vinyl Ethyl Ether and Other Vinyl Ethers
Hurd C.D., Botteron D.G.
Journal of the American Chemical Society , 1946
157.
Potassium Fluoride on Alumina. An Efficient Solid Base for Elimination, Addition, and Condensation
Yamawaki J., Kawate T., Ando T., Hanafusa T.
Bulletin of the Chemical Society of Japan , 1983
158.
A green synthesis of phenyl vinyl sulfoxide
Liu J., Qian C., Chen X.
Research on Chemical Intermediates , 2009
159.
New method of production of vinyl ether by vapor phase intramolecular dehydration of glycol ether over solid catalysts
Shimasaki Y., Ariyoshi K., Kambe H., Yano H., Ugamura S.
Journal of Molecular Catalysis A Chemical , 2006
160.
rcr_87_2_167bib160
1947
161.
Some Reactions of N-(β-Hydroxyalkyl)-carbazoles
Flowers R.G., Miller H.F., Flowers L.W.
Journal of the American Chemical Society , 1948
162.
Synthesis of N-vinylazoles from vinyl acetate without using mercury catalysts
Attaryan O.S., Baltayan A.O., Sagatelyan R.E., Takmazyan K.T.
Russian Journal of General Chemistry , 2007
163.
N,N-Divinylaniline and Its Polymerization
Chang E.Y., Price C.C.
Journal of the American Chemical Society , 1961
165.
rcr_87_2_167bib165
Attaryan
Zh. Org. Khim. , 1988
167.
Exchange of 4-chlorobenzenesulfenyl chloride between olefins
Schmid G.H., Fitzgerald P.H.
Journal of the American Chemical Society , 1971
168.
Organo-silicon Compounds. III.1 α- and β-Chloroalkyl Silanes and the Unusual Reactivity of the Latter2
170.
Reactions of aromatic sulphenyl compounds with organotin compounds
Wardell J.L., Ahmed S.
Journal of Organometallic Chemistry , 1974
172.
rcr_87_2_167bib172
Kutyrev
Zh. Obshch. Khim. , 1985
173.
A versatile vinyl sulphide synthesis using benzenesulphenyl chloride
Bartels B., Hunter R., Simon C.D., Tomlinson G.D.
Tetrahedron Letters , 1987
174.
rcr_87_2_167bib174
Karaev
Zh. Obshch. Khim. , 1994
175.
Eine neue Synthese von Vinyläthern
CHRISTOL H., CRISTAU H., SOLEIMAN M.
Synthesis , 1975
176.
177.
Synthesis of pinacol esters of 1-alkyl-1H-pyrazol-5-yl- and 1-alkyl-1H-pyrazol-4-ylboronic acids
Ivachtchenko A.V., Kravchenko D.V., Zheludeva V.I., Pershin D.G.
Journal of Heterocyclic Chemistry , 2004
180.
A New and Convenient Synthetic Method for Cyclopropyl Phenyl Sulfides
Tanaka K., Uneme H., Matsui S., Kaji A.
Bulletin of the Chemical Society of Japan , 1982
182.
rcr_87_2_167bib182
Hughes
Org. React. , 1992
185.
Solid-Phase Organic Synthesis of Aryl Vinyl Ethers Using Sulfone-Linking Strategy
Yu L., Tang N., Sheng S., Chen R., Liu X., Cai M.
Chinese Journal of Chemistry , 2012
186.
Reaction of Vinyl Ethers with Acidic Imino Compounds. A New Synthesis of Some N-Vinyl Imides
FURUKAWA J., ONISHI A., TSURUTA T.
Journal of Organic Chemistry , 1958
187.
Experimental and Theoretical Study of the 2-Alkoxyethylidene Rearrangement
Graves K.S., Thamattoor D.M., Rablen P.R.
Journal of Organic Chemistry , 2011
188.
rcr_87_2_167bib188
Morrison
J. Chem. Soc., Chem. Commun. , 1968
189.
Visible light mediated metal-free thiol–yne click reaction
Zalesskiy S.S., Shlapakov N.S., Ananikov V.P.
Chemical Science , 2016
190.
A New Method for the Preparation of Aryl Vinyl Ethers
Blouin M., Frenette R.
Journal of Organic Chemistry , 2001
191.
Direct N-vinylation of aryl and hetaryl carboxamides with trimethoxyvinylsilane
192.
Vinylation of pyridylcarboxamides with vinyltrimethoxysilane
Arsenyan P., Petrenko A., Belyakov S.
Chemistry of Heterocyclic Compounds , 2012
193.
Arsenyan Pavel, Petrenko Alla, Paegle Edgars, Belyakov Sergey
Mendeleev Communications , 2011
197.
Fast and Regioselective Heck Couplings with N-Acyl-N-vinylamine Derivatives
Hansen A.L., Skrydstrup T.
Journal of Organic Chemistry , 2005
198.
rcr_87_2_167bib198
2015
199.
Palladium-catalyzed stereocontrolled vinylation of azoles and phenothiazine
Lebedev A.Y., Izmer V.V., Kazyul'kin D.N., Beletskaya I.P., Voskoboynikov A.Z.
Organic Letters , 2002
200.
Palladium-Catalyzed Synthesis of Aryl Vinyl Sulfides via 1,3-Oxathiolanes As Vinyl Sulfide Surrogates
Schmink J.R., Dockrey S.A., Zhang T., Chebet N., van Venrooy A., Sexton M., Lew S.I., Chou S., Okazaki A.
Organic Letters , 2016
201.
rcr_87_2_167bib201
Voronkov
Zh. Org. Khim. , 1980
202.
rcr_87_2_167bib202
Trofimov
Zh. Org. Khim. , 1980
204.
The Reaction of Grignard Reagents with Bunte Salts: A Thiol-Free Synthesis of Sulfides
Reeves J.T., Camara K., Han Z.S., Xu Y., Lee H., Busacca C.A., Senanayake C.H.
Organic Letters , 2014
206.
rcr_87_2_167bib206
Markaryan
Arm. Khim. Zh. , 1985
207.
Experimental Studies on the Selective β-C–H Halogenation of Enones
Huber T., Kaiser D., Rickmeier J., Magauer T.
Journal of Organic Chemistry , 2015
208.
rcr_87_2_167bib208
Markaryan
Zh. Org. Khim. , 1983
210.
rcr_87_2_167bib210
Zeiberlikh
Zh. Org. Khim. , 1983
213.
Heterogeneous Gold-Catalyzed Selective Semireduction of Alkynes using Formic Acid as Hydrogen Source
Li S., Tao L., Wang F., Liu Y., Cao Y.
Advanced Synthesis and Catalysis , 2016
216.
Synthesis of alkenes via the Peterson reaction
Ager D.J.
Journal of the Chemical Society Perkin Transactions 1 , 1986
217.
The metathesis reaction of vinyl ethers
Thu C.T., Bastelberger T., Höcker H.
Journal of Molecular Catalysis , 1985
218.
Palladium-assisted N-alkylation of indoles: attempted application to polycyclization
Hegedus L.S., Winton P.M., Varaprath S.
Journal of Organic Chemistry , 1981
223.
The first successful direct metallation of ethene
Brandsma L., Verkruijsse H.D., Schade C., von Ragué Schleyer P.
Journal of the Chemical Society Chemical Communications , 1986
224.
Organomercury Chemistry. A Novel Synthesis of Vinyl Esters, Vinyl Ethers and Vinyl Thioethers1
225.
Reaction of 1-alkenyl and 1-alkynyl derivatives of tin and mercury with hetero-centered radicals
Russell G.A., Ngoviwatchai P., Tashtoush H., Hershberger J.
Organometallics , 1987
226.
A straightforward zinc-catalysed reduction of sulfoxides to sulfides
230.
Reduction of sulfoxides catalyzed by oxo-complexes
Cabrita I., Sousa S.C., Fernandes A.C.
Tetrahedron Letters , 2010
231.
Oxo‐Rhenium(V) Complexes Containing Heterocyclic Ligands as Catalysts for the Reduction of Sulfoxides
Sousa S.C., Bernardo J.R., Wolff M., Machura B., Fernandes A.C.
European Journal of Organic Chemistry , 2014
233.
Highly Efficient Gold Nanoparticle Catalyzed Deoxygenation of Amides, Sulfoxides, and Pyridine N-Oxides
Mikami Y., Noujima A., Mitsudome T., Mizugaki T., Jitsukawa K., Kaneda K.
Chemistry - A European Journal , 2011
235.
Mild and Efficient Reduction of Sulfoxides to Sulfides with Titanium Tetrachloride–Indium System
Yoo B.W., Choi K.H., Kim D.Y., Choi K.I., Kim J.H.
Synthetic Communications , 2003
237.
A mild, efficient, and selective procedure for the deoxygenation of sulfoxides with the TaCl5/indium system
Yoo B.W., Lee M.K., Yoon C.M.
Phosphorus, Sulfur and Silicon and the Related Elements , 2016
238.
MILD AND EFFICIENT REDUCTION OF SULFOXIDES TO SULFIDES WITH BIS-(CYCLOPENTADIENYL)TITANIUM(IV) DICHLORIDE–INDIUM SYSTEM
Yoo B.W., Choi K.H., Lee S.J., Yoon C.M., Kim S.H., Kim J.H.
Synthetic Communications , 2002
242.
I2as a mild and efficient catalyst in deoxygenation of sulfoxides with thioacetic acid
246.
Silica–PSCl3: A Mild and Efficient Reagent for Deoxygenation of Sulfoxides
Pandey L.K., Pathak U., Rao A.N.
Synthetic Communications , 2007
248.
A very useful and mild method for the deoxygenation of sulfoxide to sulfide with silica bromide as heterogeneous promoter
Mohanazadeh F., Veisi H., Sedrpoushan A., Zolfigol M.A., Golmohammad F., Hemmati S., Hashemi M.
Journal of Sulfur Chemistry , 2013
249.
Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile
Bian J., Li X., Wang N., Wu X., You Q., Zhang X.
European Journal of Medicinal Chemistry , 2017
250.
Dynamic structures of zinc, magnesium and aluminum azaallylmetal reagents
Lalonde J.J., Bergbreiter D.E., Newcomb M.
Journal of Organic Chemistry , 1986
255.
Pd-Catalyzed Inter- and Intramolecular Carbene Transfer from Group 6 Metal−Carbene Complexes1
Sierra M.A., del Amo J.C., Mancheño M.J., Gómez-Gallego M.
Journal of the American Chemical Society , 2001
256.
Über die Synthese einiger N-Vinyl-verbindungen
Schulz R.C., Hartmann H.
Monatshefte fur Chemie , 1961
258.
Notes- Synthesis of Benzyl Vinylcabamate and 3-O-Vinylcarbamoyl-D-mannitol Pentanitrate
Wolfrom M., McFadden G., Chaney A.
Journal of Organic Chemistry , 1961
259.
The Shortest Synthetic Route to Puromycin Analogues Using a Modified Robins Approach
Krishnakumar K.S., Goudedranche S., Bouchu D., Strazewski P.
Journal of Organic Chemistry , 2011
260.
An Improved Process for the Preparation of Benzyl-N-vinyl Carbamate1
Govindan C.K.
Organic Process Research and Development , 2001
261.
Intramolecular Vinylation of Secondary and Tertiary Organolithiums
Lefranc J., Fournier A.M., Mingat G., Herbert S., Marcelli T., Clayden J.
Journal of the American Chemical Society , 2012
262.
Facile Preparation of N-Vinylisobutyramide and N-Vinyl-2-pyrrolidinone
Tu S., Zhang C.
Organic Process Research and Development , 2015