Abstract
Treatment of 1-alkyl-4 and 2-alkyl-5-phenyltetrazoles 10 with t-butyllithium in tetrahydrofuran at –78 °C gives ‘dipole-stabilised’ a-lithioalkyl derivatives 2 and 3 which are readily converted into the corresponding deuteriated, silylated, alkylated, hydroxymethylated, acylated and carboxylated derivatives 5 and 11, mostly in high yield (Tables 1 and 2). Lithiation of 5-phenyl-2-trimethylsilylmethyltetrazole 10c, prepared in this way, followed by reaction with aldehydes results in Peterson olefination to give 2-alkenyltetrazoles 11g, h in good yield.
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