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Synthesis 1992; 1992(11): 1083-1084
DOI: 10.1055/s-1992-26308
short paper
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Preparation of 10-Amino-9-anthracenecarbonitriles from the Reaction of α-Cyano-o-tolunitrile and Haloarenes Under Aryne-Forming Conditions

A. Rakeeb Deshmukh* , Matt Morgan, Long Tran, Edward R. Biehl
  • *Department of Chemistry, Southern Methodist University, Dallas, Texas 75275, USA
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Publication Date:
17 September 2002 (online)

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α-Cyano-α-lithio-o-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-tetramethylbenzo-nitrile (6), most likely by the tandem addition-rearrangement pathway

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