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The mechanism of the reaction between an aziridine and carbon dioxide with no added catalyst
Author(s) -
Phung Chau,
Tantillo Dean J.,
Hein Jason E.,
Pinhas Allan R.
Publication year - 2018
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3735
Subject(s) - aziridine , chemistry , catalysis , carbon dioxide , salt (chemistry) , reaction mechanism , ammonium , kinetics , inorganic chemistry , organic chemistry , photochemistry , ring (chemistry) , physics , quantum mechanics
Abstract The mechanism of the reaction at room temperature between an unactivated 2‐alkyl aziridine and carbon dioxide to generate the corresponding oxazolidinone in glass has been studied. Theoretical calculations suggest that this reaction should not proceed at room temperature in the absence of a catalyst. In cases where a reaction was observed, kinetic studies show that the reaction displays a zero‐order dependence with respect to aziridine, indicating that free aziridine is not involved in the rate‐determining step. An ammonium salt generated in situ acts as a catalyst. The amount of this catalyst is diminutive, which prevented spectroscopic identification, and it is not readily removed from the starting material using chromatography.