PYRROLE CHEMISTRY: III. FRIEDEL-CRAFTS ISOPROPYLATION OF METHYL 2-PYRROLECARBOXYLATE
Open Access
- 1 June 1964
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 42 (6), 1279-1287
- https://doi.org/10.1139/v64-200
Abstract
The reaction between isopropyl chloride and methyl 2-pyrrolecarboxylate catalyzed by aluminum chloride has been investigated. From the reaction mixture 4-isopropyl-, 5-isopropyl-, and 4,5-diisopropyl-2-esters have been isolated and identified. It has been found that while the 4-isopropyl-2-ester rearranged to 5-isopropyl-2-ester under alkylation conditions, neither the latter nor the 4,5-diisopropyl-2-ester underwent any change. Some suggestions as to the course of the reaction are made.Keywords
This publication has 13 references indexed in Scilit:
- Synthesis and Properties of AlkylpyrrolesJournal of the American Chemical Society, 1962
- Etude des composés d'addition des acides de LEWIS. XVIII. Préparation d'esters à partir de composés d'addition des chlorures de benzoyle et de mésitoyle avec des acides de LEWIS; spectre infrarouge des composés formés par TiCl4 avec les esters méthyliques d'acides méthylbenzoïquesHelvetica Chimica Acta, 1962
- Kinetics of Three-compound Equilibrations. IV. The Isomerization of AlkylaromaticsJournal of the American Chemical Society, 1960
- Friedel-Crafts Isopropylation of Acetophenone, Methyl Benzoate and Benzoic Acid1Journal of the American Chemical Society, 1959
- Aromatic Substitution. VI. Intermediate Complexes and the Reaction Mechanism of Friedel-Crafts Alkylations and Acylations1Journal of the American Chemical Society, 1958
- The Reaction of Benzene and Toluene with Methyl Bromide and Iodide in the Presence of Aluminum Bromide; Evidence for a Displacement Mechanism in the Methylation of Aromatic Compounds1,2Journal of the American Chemical Society, 1955
- Friedel-Crafts Isopropylation of Methyl 2-Thienyl Ketone1aJournal of the American Chemical Society, 1955
- Disproportionation of Alkylbenzenes. I. Product Distribution and Rate StudiesJournal of the American Chemical Society, 1953
- Untersuchungen über Pyrrolderivate: 5. MitteilungRecueil des Travaux Chimiques des Pays-Bas, 1941
- THE DISSOCIATION CONSTANTS OF RACEMIC PROLINE AND CERTAIN RELATED COMPOUNDSThe Journal of general physiology, 1926