Oxidation of tertiary homoallylic alcohols by thallium trinitrate: fragmentation vs. ring contraction
The oxidation of tertiary homoallylic alcohols with thallium trinitrate (TTN) was investigated. The alcohols bearing an allylic methyl group lose a molecule of acetone via a fragmentation reaction that leads to isomeric secondary allylic alcohols as major products, together with their corresponding acetylated derivatives. On the other hand, treating analogous tertiary alcohols without the allylic methyl group with TTN gives indans, through a ring contraction reaction.
Saved in:
| Main Authors: | , , , , |
|---|---|
| Format: | Digital revista |
| Language: | English |
| Published: |
Sociedade Brasileira de Química
2006
|
| Online Access: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000500024 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|