Home / Publications / Synthesis of vinyl thioethers and bis-thioethenes from calcium carbide and disulfides

Synthesis of vinyl thioethers and bis-thioethenes from calcium carbide and disulfides

Konstantin Sergeevich Rodygin 1
Konstantin Sergeevich Rodygin
Yuliya Vyacheslavovna Gyrdymova 1
Yuliya Vyacheslavovna Gyrdymova
Vladimir Victorovich Zarubaev 2
Vladimir Victorovich Zarubaev
Published 2017-09-07
CommunicationVolume 27, Issue 5, 476-478
28
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Rodygin K. S., Gyrdymova Y. V., Zarubaev V. V. Synthesis of vinyl thioethers and bis-thioethenes from calcium carbide and disulfides // Mendeleev Communications. 2017. Vol. 27. No. 5. pp. 476-478.
GOST all authors (up to 50) Copy
Rodygin K. S., Gyrdymova Y. V., Zarubaev V. V. Synthesis of vinyl thioethers and bis-thioethenes from calcium carbide and disulfides // Mendeleev Communications. 2017. Vol. 27. No. 5. pp. 476-478.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2017.09.015
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.09.015
TI - Synthesis of vinyl thioethers and bis-thioethenes from calcium carbide and disulfides
T2 - Mendeleev Communications
AU - Rodygin, Konstantin Sergeevich
AU - Gyrdymova, Yuliya Vyacheslavovna
AU - Zarubaev, Vladimir Victorovich
PY - 2017
DA - 2017/09/07
PB - Mendeleev Communications
SP - 476-478
IS - 5
VL - 27
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2017_Rodygin,
author = {Konstantin Sergeevich Rodygin and Yuliya Vyacheslavovna Gyrdymova and Vladimir Victorovich Zarubaev},
title = {Synthesis of vinyl thioethers and bis-thioethenes from calcium carbide and disulfides},
journal = {Mendeleev Communications},
year = {2017},
volume = {27},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.09.015},
number = {5},
pages = {476--478},
doi = {10.1016/j.mencom.2017.09.015}
}
MLA
Cite this
MLA Copy
Rodygin, Konstantin Sergeevich, et al. “Synthesis of vinyl thioethers and bis-thioethenes from calcium carbide and disulfides.” Mendeleev Communications, vol. 27, no. 5, Sep. 2017, pp. 476-478. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.09.015.

Abstract

Bis-thioethenes and vinyl thioethers were obtained from the reaction of disulfides and calcium carbide in good to high yields using a simple synthetic procedure and common laboratory setup. The tolerance of the reaction was investigated by the examples of aliphatic, aromatic, heteroaromatic and sesquiterpenic substrates.

References

1.
Synthesis of Vinyl Selenides
Perin G., Lenardão E.J., Jacob R.G., Panatieri R.B.
Chemical Reviews, 2009
2.
Synthesis of 1,2- and 1,3-Divinylpyrrole
Settambolo R., Mariani M., Caiazzo A.
Journal of Organic Chemistry, 1998
3.
Synthesis and radical polymerization of 2-vinyldibenzothiophene
Shimomura O., Sato T., Tomita I., Suzuki M., Endo T.
Journal of Polymer Science, Part A: Polymer Chemistry, 1997
4.
Stereoselective addition of aliphatic thiols to internal alkynes in a catalytic system with palladium "nanosalt" as an active site
Orlov N.V., Chistyakov I.V., Starikova Z.A., Ananikov V.P., Beletskaya I.P.
Russian Chemical Bulletin, 2013
5.
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
6.
Synthesis and polymerization of C-vinyl- and N-vinyl-1,2,3-triazoles
Beghdadi S., Miladi I.A., Addis D., Romdhane H.B., Bernard J., Drockenmuller E.
Polymer Chemistry, 2012
7.
10.1016/j.mencom.2017.09.015_sbref0005g
Ananikov
Top. Organomet. Chem., 2013
9.
Synthesis, characterization, and polymerization of vinylmelamines
Irrgeher M., Schmidt H., Bretterbauer K., Gabriel H., Schwarzinger C.
Monatshefte fur Chemie, 2011
10.
Indium Triflate-Catalyzed Vinylation of β-Ketoesters with Acetylene Gas
11.
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
14.
Total Synthesis of the Kopsia lapidilecta Alkaloid (±)-Lapidilectine B
Pearson W.H., Lee I.Y., Mi Y., Stoy P.
Journal of Organic Chemistry, 2004
17.
Tandem photocyclization-intramolecular addition reactions of aryl vinyl sulfides. Observation of a novel [2 + 2] cycloaddition-allylic sulfide rearrangement
Dittami J.P., Nie X.Y., Nie H., Ramanathan H., Buntel C., Rigatti S., Bordner J., Decosta D.L., Williard P.
Journal of Organic Chemistry, 1992
18.
A novel entry into the bicyclo[5.4.0]undecane ring system
Rigby J.H., Sage J.M., Raggon J.
Journal of Organic Chemistry, 1982
19.
Short synthesis of bicyclo[3.2.2]nona-3,6,8-trien-2-one
Rigby J.H., Sage J.M.
Journal of Organic Chemistry, 1983
21.
Enol thioethers in synthesis. Regiocontrolled arylation via organopalladium chemistry
Trost B.M., Tanigawa Y.
Journal of the American Chemical Society, 1979
22.
Tris(trimethylsilyl)silane: an efficient hydrosilylating agent of alkenes and alkynes
Kopping B., Chatgilialoglu C., Zehnder M., Giese B.
Journal of Organic Chemistry, 1992
26.
Asymmetric oxidation of sulfides
O'Mahony G.E., Ford A., Maguire A.R.
Journal of Sulfur Chemistry, 2012
30.
Recent Developments in Sulfur-Containing Polymers
Kausar A., Zulfiqar S., Sarwar M.I.
Polymer Reviews, 2014
31.
Synthesis of sulfur-containing aryl and heteroaryl vinyls via Suzuki–Miyaura cross-coupling for the preparation of SERS-active polymers
Perez-Pineiro R., Dai S., Alvarez-Puebla R., Wigginton J., Al-Hourani B.J., Fenniri H.
Tetrahedron Letters, 2009
32.
Synthesis of gold nanocomposite via chemisorption of gold nanoparticles with poly(p-methylstyrene) containing multiple bonding groups on the chain side
Huang H., Chang C., Liu I., Tsai H., Lai M., Tsiang R.C.
Journal of Polymer Science, Part A: Polymer Chemistry, 2005
34.
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
35.
10.1016/j.mencom.2017.09.015_sbref0075b
Trofimov
Zh. Org. Khim., 1973
37.
Mild and Efficient Deoxygenation of Sulfoxides with MoCl5/Indium System
Yoo B.W., Song M.S., Park M.C.
Synthetic Communications, 2007
38.
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
40.
Stereoselective Hydrothiolation of Alkynes Catalyzed by Cesium Base:  Facile Access to (Z)-1-Alkenyl Sulfides
43.
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
44.
Method for synthesis of?,?-unsaturated sulfides from dithiolacetates
Petukhova N.P., Prilezhaeva E.N., Voropaev V.N.
Russian Chemical Bulletin, 1972
46.
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
47.
Synthesis of New Sesquiterpenoid Thio-Derivatives Based on Betulenone
Gyrdymova Y.V., Sudarikov D.V., Rubtsova S.A., Kuchin A.V.
Chemistry of Natural Compounds, 2017
48.
OLEX2: a complete structure solution, refinement and analysis program
Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A., Puschmann H.
Journal of Applied Crystallography, 2009
49.
A short history of SHELX
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography, 2007
50.
10.1016/j.mencom.2017.09.015_bib0105
Sheldrick
Acta Crystallogr.,, 2015
52.
Immunosuppressive Sesquiterpenes fromBuddleja daviddi
Zhang W., Yao Z., Zhang Y., Zhang X., Takaishi Y., Duan H.
Planta Medica, 2010
53.
Chemical analysis andin vitroantiviral and antifungal activities of essential oils fromGlechon spathulataandGlechon marifolia
Venturi C.R., Danielli L.J., Klein F., Apel M.A., Montanha J.A., Bordignon S.A., Roehe P.M., Fuentefria A.M., Henriques A.T.
Pharmaceutical Biology, 2014
54.
Screening for Antiviral Activities of Isolated Compounds from Essential Oils
Astani A., Reichling J., Schnitzler P.
Evidence-based Complementary and Alternative Medicine, 2011
55.
Chemical compositions and anti-influenza activities of essential oils from Mosla dianthera
Wu Q., Wang W., Dai X., Wang Z., Shen Z., Ying H., Yu C.
Journal of Ethnopharmacology, 2012