Abstract
The purpose of this research was to investigate the stability and reactivity of 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (PYRRO/NO) in dimethylformamide (DMF, as the reference solvent) and compare them to those obtained using different ionic liquids. The results of our experiments showed that PYRRO/NO is more stable (based on reactivity) in ionic liquid [EMIM][Ms] (with reaction yields up to 52%) than in DMF, that substitution products can be separated directly and quantitatively from the ionic liquid using a single flash-column separation, and that the ionic liquids can also be recovered and reused in a second iteration of the same reaction to achieve similar yields.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1322-1332 |
| Number of pages | 11 |
| Journal | Synthetic Communications |
| Volume | 40 |
| Issue number | 9 |
| DOIs | |
| State | Published - Jan 2010 |
| Externally published | Yes |
Funding
This work was supported by federal funds from the National Cancer Institute, National Institutes of Health (NIH) under contract HHSN261200800001E with SAIC–Frederick Inc. as well as by the Intramural Research Program of the NIH, National Cancer Institute, Center for Cancer Research.
| Funders | Funder number |
|---|---|
| National Cancer Institute’s Center for Cancer Research | |
| SAIC Frederick Inc. | |
| Author National Institutes of Health National Institutes of Health National Institutes of Health National Institutes of Health The Bev Hartig Huntington's Disease Foundation National Institutes of Health | HHSN261200800001E |
| National Institute of Health-National Cancer Institute |
Keywords
- Diazeniumdiolate
- Ionic liquid
- Nitric oxide donor
- Nucleophilic displacement
ASJC Scopus subject areas
- Organic Chemistry
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