Journal article

Publication year: 2011

Pages: 983-992

Journal: European Journal of Organic Chemistry

Volume number: 2011

Issue number: 5

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

Publisher: 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 Citation style: 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 Citation style: 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