Ab initio study on the mechanism of cycloaddition reaction of ketene with methylenimine: A new reaction scheme
- 5 August 1992
- journal article
- research article
- Published by Wiley in International Journal of Quantum Chemistry
- Vol. 43 (5) , 669-676
- https://doi.org/10.1002/qua.560430506
Abstract
The cycloaddition reaction of ketene and methylenimine, leading to 2‐azetidinone, has been studied theoretically by RHF/3‐21G and IRC. This reaction is believed to be nonsynchronous and concerted, taking place through a twisted transition state. Four π orbitals are involved in this reaction, which is a “2 × [1 + 1]”‐type cycloaddition. In the course of the reaction, rotation of the methylene group instead of oxygen in ketene was ascertained. The activated barrier is calculated to be 33.9 kcal/mol. © 1992 John Wiley & Sons, Inc.Keywords
This publication has 12 references indexed in Scilit:
- A theoretical study on ketene-olefin cycloadditions. 1. Intermolecular reactionsThe Journal of Organic Chemistry, 1990
- MCSCF study of the cycloaddition reaction between ketene and ethyleneJournal of the American Chemical Society, 1990
- Carbenoid character in transition structures for reactions of ketenes with alkenesJournal of the American Chemical Society, 1990
- Ab initio and empirical computations of mechanism and stereoselectivityPublished by Walter de Gruyter GmbH ,1989
- Theoretical study of (2 + 2) cycloadditions. Ketene with ethyleneThe Journal of Organic Chemistry, 1985
- Optimization of equilibrium geometries and transition structuresJournal of Computational Chemistry, 1982
- Cycloaddition of haloketenes to imines: A convenient synthesis of functionally substituted β-lactams and 2-pyridones.Tetrahedron Letters, 1970
- New route to .beta.-lactamsJournal of the American Chemical Society, 1969
- Studies on lactams—VIITetrahedron, 1967
- The structure of cephalosporin CBiochemical Journal, 1961