Kaplan - Shechter reaction

9 January 2009 - synthetic methods

What: Kaplan–Shechter reaction. Formation of a geminal dinitro compound from the corresponding nitronate salt with silver nitrate and sodium nitrite (DOI) . Invented by Ralph B. Kaplan and Harold Shechter in 1961. Original publication described synthesis of 1,1-dinitroethane by adding a mixture of nitroethane, sodium nitrite and aqueous sodium hydroxide to a aqueous solution of silver nitrite.

Also known as: Oxidative nitration
Made obsolete: Ter Meer reaction
Why: access to new energetic materials
Modifications: Less expensive reagents than silver for this reaction are catalytic Potassium ferricyanide (ferric to ferrous) and stoichiometric re-oxidizing agent sodium persulfate (Lee et al. 1985 DOI)
See also: Organic Chemistry of Explosives Agrawal/Hodgson