Synthesis of 3,3-dimethyl-2-phenyl-3H-pyrrole from Isopropyl Phenyl Ketoxime and Acetylene: A Side Formation of 4,4-dimethyl-5-phenyl-1-vinyl-2-pyrrolidinone as Clue to the Reaction Mechanism

Isopropyl phenyl ketoxime reacts with acetylene in the KOH/DMSO suspension (atmospheric pressure, 90°C, 4h) to afford 3,3-dimethyl-2-phenyl-3H-pyrrole (30%) and 4,4-dimethyl-5-phenyl-1-vinyl-2-pyrrolidinone (5%) that is likely originated from 4,4-dimethyl-5-phenyl-3,4-dihydro-2H-pyrrol-2-ol as the k...

Full description

Saved in:
Bibliographic Details
Published in:Mendeleev communications 2014-03, Vol.24 (2), p.100-101
Main Authors: Shabalin, Dmitrii A., Glotova, Tatyana E., Schmidt, Elena Yu, Ushakov, Igor A., Mikhaleva, Al’bina I., Trofimov, Boris A.
Format: Article
Language:English
Subjects:
Acetylene
Atmospheric pressure
Barometric pressure
Phenyls
Reaction mechanisms
Synthesis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Isopropyl phenyl ketoxime reacts with acetylene in the KOH/DMSO suspension (atmospheric pressure, 90°C, 4h) to afford 3,3-dimethyl-2-phenyl-3H-pyrrole (30%) and 4,4-dimethyl-5-phenyl-1-vinyl-2-pyrrolidinone (5%) that is likely originated from 4,4-dimethyl-5-phenyl-3,4-dihydro-2H-pyrrol-2-ol as the key reaction intermediate.
ISSN:0959-9436
DOI:10.1016/j.mencom.2014.03.012