55847-29-5Relevant academic research and scientific papers
PYRROLES FROM KETOXIMES AND ACETYLENE. 29. SYNTHESIS OF ALKYLPYRROLES FROM DIALKYLKETOXIMES AND DICHLOROETHANE BY REACTION WITH KOH-DMSO
Trofimov, B. A.,Mikhaleva, A. I.,Vasil'ev, A. N.,Korostova, S. E.,Shevchenko, S. G.
, p. 46 - 49 (2007/10/02)
Treatment of dialkylketoximes with dichloroethane and KOH-DMSO results in the formation of alkylpyrroles in 31-61percent yields.In addition, the corresponding 1-vinylpyrroles are formed simultaneously in yields up to 18percent.The corresponding 1,2-bis(alkylideneiminoxy)ethanes are obtained as side products in the reaction; they result from nucleophilic displacement of chlorine atoms by oximate anions.
PYRROLES FROM KETOXIMES AND ACETYLENE. XII. ANOMALOUS REACTIONS OF α- AND β-HYDROXY KETOXIMES
Trofimov, B. A.,Oleinikova, E. B.,Sigalov, M. V.,Skvortsov, Yu. M.,Mikhaleva, A. I.
, p. 366 - 370 (2007/10/02)
In reaction with acetylene (80 - 110 deg C, potassium hydroxide, dimethyl sulfoxide) the oximes of α- and β-hydroxy ketones R(Me)C=NOH, where R = HOCH2 (I), EtOCH2 (II), HOCH2(Me)CH (III), CH2=CHOCH2(Me)CH (IV), and Me(Me)(OH)CCH2 (V), give low yields mainly of a mixture of pyrroles not containing an oxygen atom.The following compounds were identified in the mixtures by GLC, TLC, and PMR and IR spectroscopy (compound No. of oxime and the pyrroles from which it was obtained): (II), 1-vinyl-2-methylpyrrole and 1-vinyl-2-ethoxymethylpyrrole; (III), 1-vinyl-2,3-dimethylpyrrole and 1-vinyl-2-(2-propenyl)pyrrole; (IV), 1-vinyl-2-(2-propenyl)pyrrole; (V), 1-vinyl-2-methylpyrrole.In the case of oxime (I) it was not possible to identify the pyrroles in the reaction mixture.The structures of the anomalous products are consistent with the theories that α-carbanions play an important role in the formation of the pyrrole ring from ketoximes and acetylene in the potassium hydroxide - DMSO system.
