
TY  - JOUR
A1  - Wille, Uta 
A1  - Andropof, Jilliarne 
T1  - <I>Corrigendum to</I>: Oxidation of Aromatic Alkynes with Nitrate Radicals (NO<sub>3</sub><sup>&#8226;</sup>): An Experimental and Computational Study on a Synthetically Highly Versatile Radical
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2007
VL  - 60
IS  - 7
SP  - 547
EP  - 547
KW  - 
UR  - https://doi.org/10.1071/CH07045_CO 
N2  - Addition of electro- and photochemically generated nitrate radicals, NO3&bull;, to the C&equiv;C triple bond of aromatic alkynes 9a&ndash;9h leads to formation of 1,2-diketones 10a&ndash;10h. Surprisingly, benzophenones 11a&ndash;11h are obtained as by-products, which formally result from loss of a carbon atom. Density functional studies performed with the BHandHLYP method in combination with various basis sets revealed that 1,2-diketones result from 5-endo cyclization of the initially formed vinyl radical and loss of NO&bull;. The key step to benzophenone formation is a &gamma;-cleavage at the stage of the vinyl radical with release of NO2&bull;, followed by Wolff rearrangement of the resulting &alpha;-oxo carbene. 
ER  -

