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.
Carreira E.M., Lee W., Singer R.A.
Journal of the American Chemical Society,
1995
2.
Tietze L.F., Görlitzer J.
Synthesis,
1997
3.
4.
Kim J., Shin J., Shum P., Thompson D.H.
Journal of Dispersion Science and Technology,
2001
5.
Ruck R.T., Jacobsen E.N.
Journal of the American Chemical Society,
2002
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.
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).
22.
Trofimov B.
Current Organic Chemistry,
2002
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).