660
OPARINA et al.
the boiling point of the vinyl ether and were analyzed by
Other Natural Resources, New York, 1982, p. 140.
7. Trofimov, B.A., Geteroatomnye proizvodnye atsetilena.
Novye monomery reagenty i poluprodukty (Heteroatomic
Derivatives ofAcetylene), Moscw: Nauka, 1981, 319 p.
GLC. The yields of vinyl ethers ROCH=CH are given
2
in Table 1, their physicochemical and spectral character-
istics are presented in Table 3.
8
. Trofimov, B.A., Usp. Khim., 1981, vol. 50, p. 248.
. Trofimov, B.A., Z. Chem., 1986, vol. 26, p. 41.
0. Trofimov, B.A., Zh. Org. Khim., 1986, vol. 22, p. 1991.
1. Trofimov, B.A., Zh. Org. Khim., 1995, vol. 31, p. 1368.
General procedure for vinylation of alcohols at
atmospheric pressure of acetylene. Into a reaction
flask of 100 ml capacity, equipped with an efficient re-
flux condenser connected to a trap cooled to 60°C, ther-
mometer, magnetic stirrer, and a bubbler for supplying
acetylene was charged 50 ml of DMSO, 50 mmol of al-
cohol, NaOH and CsF in amounts indicated in Table 2,
9
1
1
1
2. Mikhaleva, A.I. and Gusarova, N.K., Atsetilen: reaktsii i
proizvodnye. Bibliografiya nauchnykh trudov B.A. Tro-
fimova (Acetylene: Reactions and Derivatives. Bibliogra-
phy of Scientific Publications of B.A. Trofimov) Novosibirsk:
Izd. Ros.Akad. Nauk, 1999, 231 p.
O
the content of the flask was heated to 100 C, and acety-
lene was flown through the mixture at a rate of 2 liter per
hour. The process was monitored by GLC. On comple-
tion of the synthesis the reaction mixture was diluted with
water (200 ml), the reaction product was extracted into
the ethyl ether (4´50 ml), the extract was washed with
water (3´2030 ml), dried on K CO , combined with the
substance condensed in the trap (in case of low boiling
vinyl ethers), the solvent was removed on the rotary
evaporator, and the residue was distilled. The details of
experiments and the yields of vinyl ethers obtained are
compiled in Table 2.
1
3. Steinborn, D., Mosinski, H., Taube, R., Marschner, H., and
Bauer, J., German Patent 298775, 1990; Ref. Zh. Khim., 1993,
13N10P.
14. Steinborn, D., Mosinski, H., and Rosenstock, T.,
J. Organometal. Chem., 1991, vol. 414, p. 45.
15. Parshina, L.N., Oparina, L.A., Gorelova, O.V., Preiss, Th.,
Henkelmann, J., and Trofimov, B.A., Zh. Org. Khim., 2001,
vol. 37, p. 993.
2
3
16. Oparina, L.A., Parshina, L.N., Khilko, M.Ya., Gorelova, O.V.,
Preiss, Th., Henkelmann, J., and Trofimov, B.A., Zh. Org.
Khim., 2001, 37, p. 1629.
17. Holly, E.D., J. Org. Chem., 1959, vol. 24, p. 1752.
The study was carried out by the financial support of
the President of the Russian Federation to the leading
scientific schools (grant RF no. NSh-2241.2003.3).
18. Vasiltsov, A.M., Trofimov, B.A., and Amosova, S.V., Izv.
Akad. Nauk SSSR, Ser. Khim., 1987, p. 1785.
1
9. Ustanovlenie struktury organicheskikh soedinenii
fizicheskimi i khimicheskimi metodami (Recognition of Or-
ganic Compounds Structure with Physical and Chemical
Methods). Moscow: Khimiya, 1967.
REFERENCES
1
. Oparina, L.A., Tlegenov, R.T., Ermakova, T.G., Kuznetso-
va, N.G., Kanitskaya, L.V., Tantsyrev, A.P., and Trofi-
mov, B.A., Izv. Akad. Nauk, Ser. Khim., 2004, vol. 37, p. 232.
. Favorskii, A.E., Zh. Ros. Khim. Obshch., 1888, vol. 20,
p. 518.
20. Strosacker, C.J., Kennedy, C.C., and Pelton, E.L., US Patents
866428, 1866429, 1866430, 1932; Chem. Abstr., 1932,
1
vol. 26, p. 4345.
2
21. Miller, S.A., Acetylene. Its Properties, Manufacture and
Uses, Leningrad: Ernest Benn Ltd., 1966.
3. Reppe, W., Lieb. Ann., 1956, vol. 601, p. 81.
4. Shostakovskii, M.F., Prostye vinilovye ethery (Vinyl Ethers),
Moscow: Izd.Akad. Nauk SSSR, 1952, 280 p.
22. Shostakovskii, M.F. and Bogdanova, A.V., Izv. Akad. Nauk
SSSR.OKhN, 1952, p. 1099.
5
6
. Trofimov, B.A. Current, Org. Chem., 2002, vol. 6, p. 1121.
. Tedeschi, R.J., Acetylene-based Chemicals from Coal and
23. Shostakovskii, M.F., Mikhantev, B.I., and Neterman, V.A.,
Izv. Akad. Nauk SSSR, 1952, p. 484.
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