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Synthesis 1995; 1995(7): 827-830
DOI: 10.1055/s-1995-4016
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4-Bromopyrenes with Arylacetonitriles and 3-Cyanophthalides Under Aryne-Forming Conditions

Wei Han, Joe Tran, Hongming Zhang, Stacey Jeffrey, Dan Swartling, George P. Ford, Ed Biehl*
  • *Department of Chemistry, Southern Methodist University, Dallas, Texas 75275, USA, Fax +1(214)7684089
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Publication Date:
31 December 2000 (online)

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4-Bromopyrene reacts with arylacetonitriles under LDA-mediated aryne-forming conditions to yield rearranged 5-arylmethyl-4-pyrenecarbonitriles through 4-pyryne; no simple addition products were observed. These product ratios are in accord with predictions based on the stabilities of the respective 4-pyryne (-5.55 kcal/mol) intermediates relative to benzyne, determined by AM1 molecular orbital calculations. In addition, 4-pyryne was annulated by 3-lithiated 3-cyanophthalides to dibenzo[de,qr]naphthacene-9,14-diones which were subsequently reductively dimethylated to 9,14-dimethoxydibenzo[de,qr]naphthacenes in overall good yields.

4-pyryne - arylation - tandem addition-rearrangement - aryne stability - dibenz[de,qr]naphthacene