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Synthesis 1992; 1992(8): 765-768
DOI: 10.1055/s-1992-26222
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Synthesis of Poly(methylphenyl)acetonitriles by the Aryne Reaction

John H. Waggenspack* , Long Tran, Stephen Taylor, Lee K. Yeung, Matt Morgan, A. Rakeeb Deshmukh, Subhash P. Khanapure, Edward R. Biehl
  • *Chemistry Department, Southern Methodist University, Dallas, Texas 75275, USA
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Publikationsdatum:
17. September 2002 (online)

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Several 2-(arylmethyl) derivatives of 3,6-dimethyl- and 3,4,5,6-tetramethylbenzonitriles have been prepared in good yields most likely by a tandem addition-rearrangement reaction of the appropriate bromoarene and arylacetonitrile under aryne-forming conditions. Additionally, several 2-aryl-2-(1,4-dimethyl-2-naphthyl)acetonitriles were obtained by the usual aryne mechanism from the reaction of 2-bromo-1,4-dimethylnaphthalene and arylacetonitriles with lithium tetramethylpiperidide.