Home / Publications / Consecutive Reactions of Dialkyl Ethynyl Carbinols with Acetylene in Superbase KOH/DMSO Suspension

Consecutive Reactions of Dialkyl Ethynyl Carbinols with Acetylene in Superbase KOH/DMSO Suspension

Elena Yur'evna Schmidt 1
Elena Yur'evna Schmidt
, 
Ivan A. Bidusenko 1
Ivan A. Bidusenko
, 
Nadezhda Victorovna Zorina 1
Nadezhda Victorovna Zorina
, 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
Albina Ivanovna Mikhaleva 1
Albina Ivanovna Mikhaleva
, 
Lyudmila Vasil'evna Klyba 1
Lyudmila Vasil'evna Klyba
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2012.05.005
Published 2012-04-27
Communication , Volume 22, Issue 3, 132-133
5
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Schmidt E. Y. et al. Consecutive Reactions of Dialkyl Ethynyl Carbinols with Acetylene in Superbase KOH/DMSO Suspension // Mendeleev Communications. 2012. Vol. 22. No. 3. pp. 132-133.
GOST all authors (up to 50) Copy
Schmidt E. Y., Bidusenko I. A., Zorina N. V., Ushakov I. A., Mikhaleva A. I., Klyba L. V., Trofimov B. A. Consecutive Reactions of Dialkyl Ethynyl Carbinols with Acetylene in Superbase KOH/DMSO Suspension // Mendeleev Communications. 2012. Vol. 22. No. 3. pp. 132-133.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2012.05.005
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.05.005
TI - Consecutive Reactions of Dialkyl Ethynyl Carbinols with Acetylene in Superbase KOH/DMSO Suspension
T2 - Mendeleev Communications
AU - Schmidt, Elena Yur'evna
AU - Bidusenko, Ivan A.
AU - Zorina, Nadezhda Victorovna
AU - Ushakov, Igor Alekseevich
AU - Mikhaleva, Albina Ivanovna
AU - Klyba, Lyudmila Vasil'evna
AU - Trofimov, Boris Aleksandrovich
PY - 2012
DA - 2012/04/27
PB - Mendeleev Communications
SP - 132-133
IS - 3
VL - 22
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2012_Schmidt,
author = {Elena Yur'evna Schmidt and Ivan A. Bidusenko and Nadezhda Victorovna Zorina and Igor Alekseevich Ushakov and Albina Ivanovna Mikhaleva and Lyudmila Vasil'evna Klyba and Boris Aleksandrovich Trofimov},
title = {Consecutive Reactions of Dialkyl Ethynyl Carbinols with Acetylene in Superbase KOH/DMSO Suspension},
journal = {Mendeleev Communications},
year = {2012},
volume = {22},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.05.005},
number = {3},
pages = {132--133},
doi = {10.1016/j.mencom.2012.05.005}
}
MLA
Cite this
MLA Copy
Schmidt, Elena Yur'evna, et al. “Consecutive Reactions of Dialkyl Ethynyl Carbinols with Acetylene in Superbase KOH/DMSO Suspension.” Mendeleev Communications, vol. 22, no. 3, Apr. 2012, pp. 132-133. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.05.005.

Abstract

2-Methylbut-3-yn-2-ol, a tertiary propargylic alcohol, reacts with acetylene under pressure in superbase KOH/DMSO suspension (80°C, 1h) to afford, along with the expected vinyl ether, 2,2,4,4-tetramethyl-5-methylidene-1,3-dioxolane, 2,5-dimethyl-5-(vinyloxy)hex-3-yn-2-ol and (Z)-2-methyl-4-(2-methylbut-3-yn-2-yloxy)but-3-en-2-ol.

References

1.
(a) A. E. Favorsky, Zh. Ross. Khim. Ob-va, 1888, 20, 445 (in Russian);
2.
(b) B. A. Trofimov, in Modern Problems of Organic Chemistry, eds. R. R. Kostikov, M.A. Kuznetsov and M. S. Baird, St. -Petersburg University Press, St. Petersburg, 2010, issue 15, pp. 23-48.
3.
(a) M. F. Shostakovsky, Prostye vinilovye efiry (Vinyl Ethers), Izd. Akad. Nauk SSSR, Moscow, 1952 (in Russian) (Chem. Abstr., 1955, 49, 13287a);
5.
B. A. Trofimov, O.A. Tarasova, S.V. Amosova, M.V. Sigalov and L. M. Sinegovskaya, Zh. Org. Khim., 1986, 22, 2007 (in Russian).
6.
(a) O. A. Tarasova, B.A. Trofimov, A.V. Afonin, L.M. Sinegovskaya, N.A. Kalinina and S. V. Amosova, Zh. Org. Khim., 1991, 27, 1172 (in Russian);
7.
(b) O. A. Tarasova, B.A. Trofimov, V.V. Keiko and S. V. Amosova, Zh. Org. Khim., 1991, 27, 1180 (in Russian).
8.
A peculiar transition-metal-free cyclodimerization of propargylic alcohols to vinyl bicyclic ketals
Trofimov B.A., Schmidt E.Y., Bidusenko I.A., Ushakov I.A., Protsuk N.I., Zorina N.V., Mikhaleva A.I.
Tetrahedron, 2012
9.
Trofimov B.A., Schmidt E.Y., Skital’tseva E.V., Bidusenko I.A., Zorina N.V., Mikhaleva A.I.
Mendeleev Communications, 2012
11.
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
12.
J I. Dickstein and S. I. Miller, in The Chemistry of the Carbon–Carbon Triple Bond, part 2, ed. S. Patai, Wiley, New York, 1978, pp. 813-955.