Home / Publications / Superbase-catalysed addition of methanol to propyne and allene: an expedient synthesis of 2-methoxypropene

Superbase-catalysed addition of methanol to propyne and allene: an expedient synthesis of 2-methoxypropene

Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
Ludmila Andreevna Oparina 1
Ludmila Andreevna Oparina
Nina Kuzminichna Gusarova 1
Nina Kuzminichna Gusarova
Marina Yakovlevna Khil'ko 1
Marina Yakovlevna Khil'ko
Lidiya Nikiforovna Parshina 1
Lidiya Nikiforovna Parshina
Jochem Henkelmann 2
Jochem Henkelmann
Published 2006-01-31
CommunicationVolume 16, Issue 1, 13-14
5
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Trofimov B. A. et al. Superbase-catalysed addition of methanol to propyne and allene: an expedient synthesis of 2-methoxypropene // Mendeleev Communications. 2006. Vol. 16. No. 1. pp. 13-14.
GOST all authors (up to 50) Copy
Trofimov B. A., Oparina L. A., Gusarova N. K., Khil'ko M. Y., Parshina L. N., Henkelmann J. Superbase-catalysed addition of methanol to propyne and allene: an expedient synthesis of 2-methoxypropene // Mendeleev Communications. 2006. Vol. 16. No. 1. pp. 13-14.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1070/MC2006v016n01ABEH002198
UR - https://mendcomm.colab.ws/publications/10.1070/MC2006v016n01ABEH002198
TI - Superbase-catalysed addition of methanol to propyne and allene: an expedient synthesis of 2-methoxypropene
T2 - Mendeleev Communications
AU - Trofimov, Boris Aleksandrovich
AU - Oparina, Ludmila Andreevna
AU - Gusarova, Nina Kuzminichna
AU - Khil'ko, Marina Yakovlevna
AU - Parshina, Lidiya Nikiforovna
AU - Henkelmann, Jochem
PY - 2006
DA - 2006/01/31
PB - Mendeleev Communications
SP - 13-14
IS - 1
VL - 16
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2006_Trofimov,
author = {Boris Aleksandrovich Trofimov and Ludmila Andreevna Oparina and Nina Kuzminichna Gusarova and Marina Yakovlevna Khil'ko and Lidiya Nikiforovna Parshina and Jochem Henkelmann},
title = {Superbase-catalysed addition of methanol to propyne and allene: an expedient synthesis of 2-methoxypropene},
journal = {Mendeleev Communications},
year = {2006},
volume = {16},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2006v016n01ABEH002198},
number = {1},
pages = {13--14},
doi = {10.1070/MC2006v016n01ABEH002198}
}
MLA
Cite this
MLA Copy
Trofimov, Boris Aleksandrovich, et al. “Superbase-catalysed addition of methanol to propyne and allene: an expedient synthesis of 2-methoxypropene.” Mendeleev Communications, vol. 16, no. 1, Jan. 2006, pp. 13-14. https://mendcomm.colab.ws/publications/10.1070/MC2006v016n01ABEH002198.

Abstract

In the superbase catalytic systems ButOK/NMP, AmtOCs/NMP and KOH/DMSO, methanol readily adds to propyne and allene at 100–120 °C and atmospheric pressure to afford 2-methoxypropene in 80–97% yield with 75–94% methanol conversion.

References

1.
Catalytic, Enantioselective Acetone Aldol Additions with 2-Methoxypropene
Carreira E.M., Lee W., Singer R.A.
Journal of the American Chemical Society, 1995
4.
Acid- and Oxidatively-Labile Vinyl Ether Surfactants: Synthesis and Drug Delivery Applications
Kim J., Shin J., Shum P., Thompson D.H.
Journal of Dispersion Science and Technology, 2001
5.
Asymmetric Catalysis of Hetero-Ene Reactions with Tridentate Schiff Base Chromium(III) Complexes
6.
10.1070/MC2006v016n01ABEH002198_bib5
Agre
Khim.-Farm. Zh., 1983
7.
10.1070/MC2006v016n01ABEH002198_bib6
Agre
Khim.-Farm. Zh., 1984
8.
O. N. Temkin, G. K. Shestakov, I. V. Kalechits, A. M. Taber, L. D. Kuprijanova and N. I. Anokhina, Ger. Patent, DD 267629, C07C, 1989 (Chem. Abstr., 1990, 112, 54986).
9.
O. N. Temkin, G. K. Shestakov, L. D. Kuprianova, A. M. Taber, S. S. Zhukovskij and V. E. Vasserberg, Ger. Patent, DD 265289, C07C, 1989 (Chem. Abstr., 1990, 112, 54987).
10.
J. H. Teles, N. Rieber, K. Breuer, D. Demuth, H. Hibst and A. Hagemeyer, Eur. Patent, EP 0887330, C07C, 1998 (Chem. Abstr., 1999, 130, 83190).
11.
J. H. Teles, N. Rieber, K. Breuer, C. W. Rieker, D. Demuth, H. Hibst and A. Hagemeyer, Eur. Patent, EP 0887331, C07C, 1998 (Chem. Abstr., 1999, 130, 83191).
12.
J. H. Teles, N. Rieber, K. Breuer, D. Demuth and H. Hibst, Eur. Patent, EP 0887332, C07C, 1998 (Chem. Abstr., 1999, 130, 83192).
13.
Zinc Silicates: Very Efficient Heterogeneous Catalysts for the Addition of Primary Alcohols to Alkynes and Allenes
Breuer K., Teles J.H., Demuth D., Hibst H., Schäfer A., Brode S., Domgörgen H.
Angewandte Chemie - International Edition, 1999
14.
J. Schroeder, S. Boeck and K. Ebel, Eur. Patent, EP 0776879, C07C, 1997 (Chem. Abstr., 1998, 127, 81155).
15.
J. H. Teles, N. Rieber, K. Breuer, D. Demuth, H. Hibst, H. Etzrodt and U. Rheude, World Patent, WO 9858894, C07C, 1998 (Chem. Abstr., 1999, 130, 68148).
16.
J. H. Teles, N. Rieber, K. Breuer, D. Demuth, H. Hibst, H. Etzrodt and U. Rheude, US Patent, US 6211416, C07C, 1999 (Chem. Abstr., 1999, 130, 68148).
17.
S. Krill, S. Kretz, V. Hafner and G. Markowz, US Patent, US 6566559, 2001 (Chem. Abstr., 2003, 136, 55543).
18.
10.1070/MC2006v016n01ABEH002198_bib13
Wang
Chem. Commun., 1938
19.
B. A. Trofimov, Geteroatomnye proizvodnye atsetilena. Novye polifunktsional’nye monomery, reagenty i poluprodukty (Heteroatomic Derivatives of Acetylene. New Polyfunctional Monomers, Reagents and Intermediates), Nauka, Moscow, 1981 (in Russian).
20.
B. A. Trofimov and S. V. Amosova, Divinilsul’fid i ego proizvodnye (Divinyl Sulfide and Its Derivatives), Nauka, Novosibirsk, 1983 (in Russian).
21.
B. A. Trofimov and A. I. Mikhaleva, N-Vinilpirroly (N-Vinylpyrroles), Nauka, Novosibirsk, 1984 (in Russian).
23.
10.1070/MC2006v016n01ABEH002198_bib18
Trofimov
2004
24.
J. Henkelmann, H. Becker, J. Aiscar, B. A. Trofimov, N. K. Gusarova and L. A. Oparina. US Patent, US 6504064, C07C, 2002. (Chem. Abstr., 2003, 136, 69592).