The benzil rearrangement reaction: trapping of a hitherto minor product and its application to the development of a selective cyanide anion indicator.
The isolation and characterization of an intermediate from the benzil-cyanide reaction is reported. The use of this trapping chemistry to produce a chemical indicator for the cyanide anion is described. It relies on the synthesis and reaction of a pi-extended analogue of benzil. Addition of tetrabutylammonium cyanide to organic solutions of this species, referred to as compound 3 in the text, gives rise to a dramatic change in both color and fluorescence properties.
Sessler
Jonathan L
JL
Department of Chemistry and Biochemistry and Institute for Cellular and Molecular Biology, The University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712-0165, USA. sessler@mail.utexas.edu
Cho
Dong-Gyu
DG
D000838:Anions / Q000032:analysis; D003486:Cyanides / Q000737:chemistry*; D005453:Fluorescence; D015394:Molecular Structure; D010658:Phenylglyoxal / Q000031:analogs & derivatives* / Q000737:chemistry
D000838:Anions; D003486:Cyanides; D010658:Phenylglyoxal; C006697:benzil