The metalation chemistry of several 1‐substituted‐1 H ‐1,2,4‐triazoles has been investigated. When various alkyl groups were incorporated in the 1‐position, lithiation proceeded exclusively at C‐5. The 1‐trityl‐, 1‐methyl‐, and 1‐benzyl‐5‐lithio‐1,2,4‐triazoles were stable at −78° and reacted cleanly with a variety of electrophiles. The 1‐benzyl and 1‐methyl derivatives were synthetically more versatile and could be successfully utilized to prepare several examples of the previously unknown 1,2,4‐triazol‐5‐yl phosphonates.
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Anderson et al. (1986) studied this question.