Home / Publications / 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

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

Dmitrii Andreevich Shabalin 1
Dmitrii Andreevich Shabalin
, 
Tat'yana Evgen'evna Glotova 1
Tat'yana Evgen'evna Glotova
, 
Elena Yur'evna Schmidt 1
Elena Yur'evna Schmidt
, 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
Albina Ivanovna Mikhaleva 1
Albina Ivanovna Mikhaleva
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2014.03.012
Published 2014-02-21
Communication , Volume 24, Issue 2, 100-101
11
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Shabalin D. A. et al. 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 // Mendeleev Communications. 2014. Vol. 24. No. 2. pp. 100-101.
GOST all authors (up to 50) Copy
Shabalin D. A., Glotova T. E., Schmidt E. Y., Ushakov I. A., Mikhaleva A. I., Trofimov B. A. 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 // Mendeleev Communications. 2014. Vol. 24. No. 2. pp. 100-101.
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TY - JOUR
DO - 10.1016/j.mencom.2014.03.012
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2014.03.012
TI - 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
T2 - Mendeleev Communications
AU - Shabalin, Dmitrii Andreevich
AU - Glotova, Tat'yana Evgen'evna
AU - Schmidt, Elena Yur'evna
AU - Ushakov, Igor Alekseevich
AU - Mikhaleva, Albina Ivanovna
AU - Trofimov, Boris Aleksandrovich
PY - 2014
DA - 2014/02/21
PB - Mendeleev Communications
SP - 100-101
IS - 2
VL - 24
ER -
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@article{2014_Shabalin,
author = {Dmitrii Andreevich Shabalin and Tat'yana Evgen'evna Glotova and Elena Yur'evna Schmidt and Igor Alekseevich Ushakov and Albina Ivanovna Mikhaleva and Boris Aleksandrovich Trofimov},
title = {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},
journal = {Mendeleev Communications},
year = {2014},
volume = {24},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2014.03.012},
number = {2},
pages = {100--101},
doi = {10.1016/j.mencom.2014.03.012}
}
MLA
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Shabalin, Dmitrii Andreevich, et al. “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.” Mendeleev Communications, vol. 24, no. 2, Feb. 2014, pp. 100-101. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2014.03.012.

Abstract

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.

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