| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 66940 | Journal of Molecular Catalysis A: Chemical | 2010 | 4 Pages |
Al(OTf)3 generates blue carbocations from retinyl acetate. The mechanism appears to be exclusively water-derived induced Brønsted acidity causing loss of acetic acid, not Lewis-mediated acetate abstraction. Dry DCM (1 ppm water) avoided water interference. The hindered base 2,6-di-tert-butylpyridine, used to distinguish between Lewis- and Brønsted acidity, was also probed. The results implicate a possible mechanism for similar transformations involving carbocations.
Graphical abstractRetinyl acetate liberates intense blue carbocations with Brønsted acids. Al(OTf)3 also generates such carbocations apparently exclusively via water-derived induced Brønsted acidity (loss of acetic acid) as opposed to the Lewis acid acting as an acetate abstractor.Figure optionsDownload full-size imageDownload high-quality image (112 K)Download as PowerPoint slide
