Enamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, 8-18-8-8. CH,I 25°C CH3 reflux CH3 CH3 Product of Product of (racemic) Galkylation Nalkylation Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.

Enamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, 8-18-8-8. CH,I 25°C CH3 reflux CH3 CH3 Product of Product of (racemic) Galkylation Nalkylation Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.40P: Enamines normally react with methyl iodide to give two products: one arising from alkylation at...

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