Synfacts 2008(4): 0368-0368  
DOI: 10.1055/s-2008-1042843
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Using the Benzil Rearrangement Reaction To Detect Cyanide

Contributor(s): Timothy M. Swager, Jan M. Schnorr
J. L. Sessler*, D.-G. Cho
The University of Texas at Austin, USA
Further Information

Publication History

Publication Date:
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.