Abstract
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.
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