High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and Norbornadiene
Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, 4702, Australia
*
Author to whom correspondence should be addressed.
Molecules 2000, 5(12), 1417-1428; https://doi.org/10.3390/51201417
Received: 3 November 2000 / Accepted: 6 November 2000 / Published: 22 December 2000
Ab initio and DFT quantum chemical calculations have been applied to a study of the Diels-Alder reaction of o-benzoquinone as diene and norbornadiene as dienophile. Transition states for the different reactions are located and activation energies estimated. The prefered exo-π-facial selectivity and exo,endo-stereoselectivity exhibited in this cycloaddition are readily predicted using RHF/3-21G or higher levels of calculations. Differences between experimentally observed results and calculations may be explained by the postulation of a second, nonconcerted biradical mechanism leading to formation of hetero Diels-Alder products.
View Full-Text
▼
Show Figures
Figure 1
This is an open access article distributed under the Creative Commons Attribution License
MDPI and ACS Style
Margetic, D.; Johnston, M.R.; Warrener, R.N. High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and Norbornadiene. Molecules 2000, 5, 1417-1428.
Show more citation formats
Search more from Scilit
