A

Claim:
Florida Woman Calls Police Worried Retro-Dieckmann Reaction Carried Out in Thermos Might Explode After Improperly Following Tutorial

Rating:
False

Euphemism run amok. The Florida woman in question was definitely not carrying out a retro-Dieckmann reaction.

The Dieckmann Condensation reaction is a base-catalyzed intramolecular condensation of a diester. The reaction works well to produce 5 or 6 membered cyclic ß-keto esters. This condensation is usually affected with sodium alkoxide in an alcoholic solvent. Should the product have an enolizable proton the yields are typically good. Should there be poor enolizable protons; it would be expected that the reverse reaction to compete. Historically used as a ring opening mechanism under basic conditions, the retro-Dieckmann reaction is used to relieve ring strain. After improperly storing the Dieckmann condensation reaction, the woman allegedly found the side reactions of this mechanism to open rings releasing energy, ultimately ruining the thermos. In practice the Dieckmann condensation reaction acts to produce a 5 or 6 membered cyclic beta-keto ester. Unfortunately for the Florida woman, this product can be effected with sodium alkoxide. The Dieckmann Condensation reaction is quite similar to the Claisen Condensation and can be used in a One-Pot Synthesis of certain acids from esters.


Organic Chemistry Portal: Dieckmann Condensation