Quote: Originally posted by UnintentionalChaos ![](images/xpblue/lastpost.gif) | The suggestion of alkylating a lower nitro compound is interesting. You'd have to use stoichiometric strong base at low temps I suppose, but appending
n-halopropane to nitromethane seems like a good way to go. |
Do you have any reference for that?
Generally nitronates that are not additionally stabilized, such as the nitromethane derived nitronate, get O-alkylated rather than C-alkylated
(exceptions are substitutions via SRN1). A dianion can be made from nitroalkanes (e.g., alpha lithiated nitronate) and this can be monoalkylated under
undesirable conditions (in HMPA!). There is an Angewandte article about it, posted somewhere on the forum, but obviously this is of no use for the
original poster here. Additionally stabilized nitronates, like the ethyl nitroacetate derived one, can be C-alkylated with good selectivity.
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