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The Benzil Rearrangement Reaction:  Trapping of a Hitherto Minor Product and Its Application to the Development of a Selective Cyanide Anion Indicator

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journal contribution
posted on 03.01.2008, 00:00 by Jonathan L. Sessler, Dong-Gyu Cho
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 π-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.