Preparation of 10-Amino-9-anthracenecarbonitriles from the Reaction of α-Cyano-o-tolunitrile and Haloarenes Under Aryne-Forming Conditions

α-Cyano-α-litbio-α-tolunitrile (4) undergoes cycloaddition with various methoxy substituted arynes 2 to yield 10-amino-9-anthracene-carbonitriles 5. In contrast, 3,4,5,6-tetramethylbenzyne (2f) reacts with 4 to yield 2-(2-cyanophenyl)methyl-3,4,5,6-tetramethylbenzonitrile (6), most likely by the tandem addition-rearrangement pathway