A study was made of the diene condensation of the cis and trans isomers of 2-bromovinyl ethyl ether with hexachlorocyclopentadiene and with cyclopentadiene. Under the conditions studied only cis-2-bromovinyl ethyl ether forms an adduct with hexachlorocyclopentadiene.
The cis and trans isomers of 2-bromovinyl ethyl ether were brought into reaction with acetaldehyde diethyl acetal. 2-Bromo-1,1,3-triethoxybutane was isolated and characterized, and its structure was proved.
2-Bromovinyl ethyl, 2-bromovinyl isopropyl, and 2-bromovinyl butyl ether were brought into reaction with phosphorus pentachloride, and the resulting 2-alkoxy-1-bromovinylphosphonic dichlorides were isolated and characterized.
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D. A. Dorp, J. F. Arens, and O. Stephenson, Recueil trav. chim.,70, 289 (1951);74, 271 (1955);77, 753 (1958);78, 284 (1959); I. N. Nazarov and A. V. Semenovskii, Izv. AN SSSR. Otd. khim. n., 1959, 1772.
M. F. Shostakovskii, A. V. Bogdanova, and T. M. Ushakova, Izv. AN SSSR. Otd. khim. n., 1957, 1245; 1960, 1286; M. F. Shostakovskii, A. V. Bogdanova, and A. N. Volkov, Zh. obshch. khimii,31, 2096 (1961); Izv. AN SSSR. Otd. khim. n., 1961, 2072; 1962, 346.
R. J. Hoaglin and D. H. Hirsh, J. Amer. Chem. Soc.,71, 3468 (1949); M. F. Shostakovskii and A. V. Bogdanova, Dokl. AN SSSR100, 89 (1955); Japanese Pat. 4678, June 18, 1956; RZhKhim, No. 4, 12752 (1959).
K. N. Anisimov and A. N. Nesmeyanov, Izv. AN SSSR. Otd. khim. n., 1954, 610.
M. F. Shostakovskii, I. I. Guseinov, L. I. Shmonina, R. S. Vasil'ev, and B. V. Lopatin, Zh. obshch. khimii.,9, 2836 (1960).
I. N. Nazarov, Zh. A. Krasnaya, and V. P. Vinogradov, Zh. obshch. khimii,2, 460 (1958).
M. F. Shostakovskii and V. A. Gladyshevskaya, Izv. AN SSSR. Otd. khim. n., 1955, 344.
L. Claisen, Ber.,44, 1164 (1911).
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Shostakovskii, M.F., Shmonina, L.I. & Tikhomirova, I.M. Reactivity of alkyl 2-halovinyl ethers. Russ Chem Bull 12, 2019–2022 (1963). https://doi.org/10.1007/BF00844001