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Synlett 1990; 1990(7): 413-414
DOI: 10.1055/s-1990-21110
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N-(α-Lithioalkyl)tetrazoles and their Reactions with Electrophiles

Christopher J. Moody* , Charles W. Rees, Richard G. Young
  • *Department of Chemistry, Imperial College of Science, Technology and Medicine, South Kensington, London SW7 2AY, England
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Publication Date:
08 March 2002 (online)

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Treatment of 1- and 2-alkyl-5-phenyltetrazoles with tert-butyllithium in tetrahydrofuran at -78 °C gives "dipole-stabilised" α-lithioalkyl derivatives which are readily converted into the corresponding deuterated, silylated, alkylated, hydroxymethylated, acylated and carboxylated derivatives, mostly in high yield. Lithiation of 5-phenyl-2-trimethylsilylmethyltetrazole followed by reaction with aldehydes results in Peterson olefination to give 2-alkenyltetrazoles in good yield.

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