76892-11-0Relevant articles and documents
PYRROLES FROM KETOXIMES AND ACETYLENE. 24. ACIDIC HYDROLYSIS OF 1-VINYLPYRROLES
Trofimov, B.A.,Korostova, S.E.,Mikhaleva, A.I.,Sobenina, L.N.,Vasil'ev, A.N.
, p. 1257 - 1265 (1982)
The hydrolysis of 2-methyl-, 2-phenyl-, and 3-methyl-2-phenyl-1-vinylpyrroles and 1-vinyl-4,5,6,7-tetrahydroindole in the presence of HCl, H2SO4, NH2OH*HCl, acetic acid, and H2O2 in aqueous, aqueous dioxane, and aqueous alcohol solutions leads to oligomers with complex structures and compositions, viz., products of acidic catalytic and oxidative condensation of the starting compounds and the resulting pyrroles both with one another and with the liberated acetaldehyde. 2-Phenylpyrrole was obtained in 52percent yield from 1-vinyl-2-phenylpyrrole by hydrolysis in a dilute (0.5percent) solution with excess NH2OH*HCl, which ties up the acetaldehyde.
PYRROLES FROM KETOXIMES AND ACETYLENE. XV.* ELECTROPHILIC ADDITION OF ALCOHOLS TO N-VINYLPYRROLES
Trofimov, B. A.,Korostova, S. E.,Sobenina, L. N.,Trzhtsinskaya, B. V.,Mikhaleva, A. I.,Sigalov, M. V.
, p. 1674 - 1677 (2007/10/02)
N-Vinylpyrroles add alcohols in the presence both of protic and of aprotic acids or their combinations.The reaction occurs according to the Markovnikov rule with the formation of N-(α-alkoxyethyl)pyrroles, which do not exhibit a tendency toward disproportionation and alcoholysis.The addition rate of the alcohols depends on the donating strength of the alcohol radical and decreases with its increase.At elevated temperatures polymerization of N-vinylpyrroles is observed.The character and form of the kinetic curves at 76-78 deg C indicate that the process is irreversible.
