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Synlett 1993; 1993(11): 843-846
DOI: 10.1055/s-1993-22628
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On the Regiochemistry of Cycloaddition of Unsymmetrical Aryne with Nitrone Remarkable Effect of Trialkylsilyl Substituent

Takashi Matsumoto* , Tsukasa Sohma, Shoichiro Hatazaki, Keisuke Suzuki
  • *Department of Chemistry, Keio University, Hiyoshi, Yokohama 223, Japan
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Publication Date:
19 March 2002 (online)

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Regioselectivity of the aryne-nitrone cycloaddition was studied. Various unsymmetrical arynes with C(3)-substituent were generated at -78 °C by halogen-lithium exchange of ortho-haloaryl triflate and trapped with a nitrone. The sense and magnitude of the regio-controlling effect posed by the substituent is discussed based on the electronic and steric grounds by assuming the non-synchronous, charge-controlled transition state. The trialkylsilyl group, by its strong electron-releasing property, poses a remarkable effect on the regioselectivity.