Nitric oxide reacts with methoxide.
Despite over a century of reports to the contrary, sodium methoxide 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 [CH3O-N(O)=NO-] that decomposes to formaldehyde and nitrous oxide. Sodium formate forms from the aldehyde via a Cannizzaro reaction. Carboxylate salts have similarly been obtained by exposing sodium benzylate and sodium neopentoxide to NO in dioxane solution. Accordingly, sodium trimethylsilanoate should be considered as a substitute for sodium methoxide as the base used to accomplish the replacement of active hydrogens by the diazeniumdiolate functional group via the Traube reaction.
Derosa
Frank
F
Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick, Frederick, Maryland 21702, USA.
Keefer
Larry K
LK
Hrabie
Joseph A
JA
D000431:Ethanol / Q000031:analogs & derivatives / Q000737:chemistry; D000432:Methanol / Q000737:chemistry*; D015394:Molecular Structure; D009569:Nitric Oxide / Q000737:chemistry*; D020160:Sodium Benzoate / Q000737:chemistry
C098088:sodium ethoxide; D009569:Nitric Oxide; D000431:Ethanol; D020160:Sodium Benzoate; D000432:Methanol