Abstract
Reported here are studies directed at understanding the mechanism of tertiary amine addition to hexadehydro-Diels-Alder (HDDA)-generated benzynes. Tertiary amines are presumed to engage benzynes by generation of a zwitterionic intermediate. Simple trialkylamines undergo intermolecular protonation by a protic nucleophile to give an aryl ammonium intermediate that is then dealkylated. Amines containing acidified β-protons undergo an intramolecular elimination to give the aniline and an alkene. Finally, amino alcohols react at either of their N- or O atoms, depending upon the extent of internal hydrogen bonding.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 5705-5708 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 19 |
| Issue number | 20 |
| DOIs | |
| State | Published - Oct 20 2017 |
Bibliographical note
Publisher Copyright:© 2017 American Chemical Society.
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