In:
Progress in Reaction Kinetics and Mechanism, SAGE Publications, Vol. 45 ( 2020-01), p. 146867831982574-
Abstract:
The mechanistic nature of a [3+2] cycloaddition reaction involving zwitterionic species has been investigated, and the changes of electron density related to the O–C and C–C bond formation along the intrinsic reaction coordinate have been characterized. This polar [3+2] cycloaddition reaction, which takes place through a non-concerted two-stage one-step mechanism, proceeds with a moderate Gibbs free activation energy of 21 kcal mol −1 . The reaction begins by the creation of a pseudoradical centre at the central carbon, first on the dimethyl acetylenedicarboxylate, and second on the nitrone framework. This immediately favours the formation of the first O–C single bond by donation of some electron density of the oxygen atom lone pairs, which represents the most attractive centre in this cycloaddition reaction.
Type of Medium:
Online Resource
ISSN:
1468-6783
,
1471-406X
DOI:
10.1177/1468678319825742
Language:
English
Publisher:
SAGE Publications
Publication Date:
2020
detail.hit.zdb_id:
2018085-8
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