Despite over a century of reports to the contrary, sodiummethoxide has been found to react with nitric oxide (NO).The reaction, whose final organic product is sodium formate,is postulated to occur via an intermediate O-bound diazeniumdiolate [CH
3O-N(O)=NO
-] that decomposes to formaldehyde and nitrous oxide. Sodium formate forms from thealdehyde via a Cannizzaro reaction. Carboxylate salts havesimilarly been obtained by exposing sodium benzylate andsodium neopentoxide to NO in dioxane solution. Accordingly, sodium trimethylsilanoate should be considered as asubstitute for sodium methoxide as the base used to accomplish the replacement of active hydrogens by thediazeniumdiolate functional group via the Traube reaction.
