Journalartikel

Jahr der Veröffentlichung: 2011

Seiten: 983-992

Zeitschrift: European Journal of Organic Chemistry

Bandnummer: 2011

Heftnummer: 5

DOI Link: https://doi.org/10.1002/ejoc.201001365

Verlag: Wiley

Abstract: 

We present an analysis of the well‐known normal‐ and inverse‐electron‐demand hetero‐Diels–Alder reaction involving 1,2,4‐triazine, 1,3‐oxazin‐6‐one, and 1,4‐oxazin‐2‐one, with alkenes and alkynes, utilizing density functional theory (DFT) at the SCS‐MP2/cc‐pVDZ//B3LYP/6‐31G(d) level to establish a theoretical status quo for synthetic practioners regarding the relative reactivities and stereochemical outcomes for these useful heterocycles. The results suggest that in the unsubstituted cases 1,2,4‐triazine is less reactive in comparison to 1,3‐oxazin‐6‐one and 1,4‐oxazin‐2‐one for both reaction modes, whereas the cycloaddition regioselectivities depend largely on the diene. For example, 1,3‐oxazin‐6‐one leads to kinetic meta isomers, in comparison to 1,2,4‐triazine and 1,4‐oxazin‐2‐one, which give rise to para isomers.

Harvard-Zitierstil: Rooshenas, P., Hof, K., Schreiner, P. and Williams, C. (2011) 1,2,4‐Triazine vs. 1,3‐ and 1,4‐Oxazinones in Normal‐ and Inverse‐Electron‐Demand Hetero‐Diels–Alder Reactions: Establishing a Status Quo by Computational Analysis, European Journal of Organic Chemistry, 2011(5), pp. 983-992. https://doi.org/10.1002/ejoc.201001365

APA-Zitierstil: Rooshenas, P., Hof, K., Schreiner, P., & Williams, C. (2011). 1,2,4‐Triazine vs. 1,3‐ and 1,4‐Oxazinones in Normal‐ and Inverse‐Electron‐Demand Hetero‐Diels–Alder Reactions: Establishing a Status Quo by Computational Analysis. European Journal of Organic Chemistry. 2011(5), 983-992. https://doi.org/10.1002/ejoc.201001365