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Using the Benzil Rearrangement Reaction To Detect Cyanide
J. L. Sessler*, D.-G. Cho
The University of Texas at Austin, USA
19 March 2008 (online)
The authors report the isolation of the mandelonitrile benzoate derivative 5 as the product of the benzil rearrangement reaction of 1 run in an aprotic solvent (i.e., acetonitrile, trichloromethane, or ethyl acetate). In the product 5, the conjugation pathway between the two aryl carbonyl groups originally present in 1 is severed causing a large hypsochromic shift (Δ λmax = 56 nm). This effect was exploited by using 1 as a cyanide indicator.