Effect of the leaving group on the reaction of 2-aminopyrroles with electron deficient heteroaromatic azadienes: substitution by addition-elimination versus cycloaddition |
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| Authors: | Michael De Rosa David Arnold |
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| Institution: | a Department of Chemistry, The Pennsylvania State University Delaware County, 25 Yearsley Mill Road, Media, PA 19063, USA
b Research Institute of Matej Bel University, Cesta na amfiteáter 1, SK-97400 Banská Bystrica, Slovak Republic |
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| Abstract: | When a good leaving group is present in the heteroaromatic azadiene, reaction with 2-aminopyrroles occurs by substitution by addition-elimination instead of cycloaddition. This novel reaction is sensitive to steric effects and takes place in 2-amino-1-methylpyrrole at C-5 and the exo amino group but at C-3 in 2-amino-1-t-butylpyrrole. |
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| Keywords: | 2-Aminopyrroles Substitution Addition-elimination Ambident behaviour Zwitterions Meisenheimer complex Leaving group Steric effects |
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