Direct Regioselective Esterification at O-2 of β-Cyclodextrin and Hydrolysis by Neighboring-group Participation
A simple and efficient strategy for direct regioselective esterification at O-2 of β-cyclodextrin was developed by using the combination of N,N'-carbonyldiimidazole and carbonate buffer in 1,4-dioxane, which does not require large amounts of polar organic solvents such as DMF, toxic solvents su...
Saved in:
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Wiley
2012-01-01
|
| Series: | E-Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2012/398683 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Summary: | A simple and efficient strategy for direct regioselective esterification at O-2 of β-cyclodextrin was developed by using the combination of N,N'-carbonyldiimidazole and carbonate buffer in 1,4-dioxane, which does not require large amounts of polar organic solvents such as DMF, toxic solvents such as CH3CN, or flammable bases such as NaH. Moreover, their hydrolyses by neighboring-group participation were observed. Mono-2-tosyl-β-cyclodextrin was liable to epoxidation, while mono-2-(p-methylbenzoyl)-β-cyclodextrin liable to isomerization. They had different mechanisms of hydrolysis. |
|---|---|
| ISSN: | 0973-4945 2090-9810 |