Silver trinitromethane

Silver trinitromethane undergoes addition to adamantyl (Ad) halides,31 methyl iodide, and trinitromethyl iodide (Scheme 1.7).32... 

The intermolecular alkylation of metallo nitronates with various alkyl halides is limited. The addition of methyl iodide to the silver salt of an aryl nitro-methane provides the corresponding methyl nitronate in moderate yield (Eq. 2.13) (150), which has also been extended to the silver salt of trinitromethane (Scheme 2.16) (151-153). However, in the case of primary halides, both O- and C-alkylation are observed. For secondary and tertiary halides, only O-alkylation is observed, but in low yields. Unfortunately, under the reaction conditions, the starting alkyl halide can undergo dehydrohalogenation to provide the corresponding alkene, which then undergoes [3+2] cycloaddition with the alkyl nitronate. 

W. S. Reich [96] prepared aromatic derivatives of trinitromethane (of the type IV) by acting with the silver salt of nitroform on ar-alkyl chlorides, as for example p- nitrobenzyl chloride ... 

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