Open AccessCS2/CO2Utilization Using Mukaiyama Reagent as a (Thio)carbonylating Promoter: A Proof-of-Concept Study
Author(s) -
Abdussalam K. Qaroush,
Ala’a F. Eftaiha,
Amneh H. Smadi,
Khaleel I. Assaf,
Feda’a M. Al-Qaisi,
Fatima Alsoubani
Publication year - 2022
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.2c01774
Subject(s) - reagent , chemistry , thio , enol , solvent , ethylene , fourier transform infrared spectroscopy , iodide , photochemistry , medicinal chemistry , organic chemistry , catalysis , chemical engineering , engineering
We report on the reaction of ethylene-terminated heteroatoms (C 2 X; X = N, O, and S) with CS 2 /CO 2 using Mukaiyama reagent (2-chloro-1-methylpyridinium iodide, CMPI) as a promoter for the preparation of imidazolidin-2-one, oxazolidin-2-one, 1,3-dioxolan-2-one, 1,3-dithiolan-2-one, and their thione counterparts at ambient temperature and pressure. Spectroscopic measurements, viz. , 1 H/ 13 C nuclear magnetic resonance (NMR) and ex situ attenuated total reflectance-Fourier transform infrared (ATR-FTIR) spectroscopy methods verified the reaction of CS 2 /CO 2 with the ethylene-based substrates and subsequently the formation of cyclic products. The experimental data indicated the formation of the enol -form of imidazolidin-2-one and oxazolidin-2-one, while the keto -form was obtained for their thione correspondents. Furthermore, density functional theory calculations revealed the stability of the keto - over the enol -form for all reactions and pointed out the solvent effect in stabilizing the latter.