Differences in regioselectivity were observed during the SNAr reaction of amines with unsymmetrical 3,5-dichloropyrazines. This study revealed that when the 2-position of the pyrazine was occupied with an electron-withdrawing group (EWG), nucleophilic attack occurred preferentially at the 5-position. When the 2-position was substituted with an electron-donating group (EDG), nucleophilic attack occurred preferentially at the 3-position. These results are reported along with a computational rationale for the experimental observations based on the Fukui index at the reacting centers. © 2013 American Chemical Society.
CITATION STYLE
Scales, S., Johnson, S., Hu, Q., Do, Q. Q., Richardson, P., Wang, F., … McAlpine, I. (2013). Studies on the regioselective nucleophilic aromatic substitution (S NAr) reaction of 2-substituted 3,5-dichloropyrazines. Organic Letters, 15(9), 2156–2159. https://doi.org/10.1021/ol4006695
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