| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5220846 | Tetrahedron | 2011 | 6 Pages |
Abstract
N[β-(Hetero)arylvinyl] ketenimines and carbodiimides bearing adequately positioned 1,3-dioxolane functions experience a new class of tandem process consisting of a 6Ï electrocyclic ring closure followed by a rare retro-cheletropic ene reaction, the extrusion of 2-carbena-1,3-dioxolane. This mechanistic sequence is supported by a computational study using DFT methods, showing that the simultaneous recovery of aromaticity at two rings is the clue for the low energy barrier of the retro-cheletropic step. Moreover, the highly exergonic decomposition of 2-carbena-1,3-dioxolane into CO2 plus ethylene contribute to the success of the tandem sequences.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Mateo Alajarin, Marta Marin-Luna, Maria-Mar Ortin, Pilar Sanchez-Andrada, Angel Vidal,