Doering-LaFlamme Reaction

The Doering-LaFlamme allene synthesis is a reaction in organic chemistry that converts alkenes to the corresponding allenes by the insertion of a carbon atom.

Doering-LaFlamme Reaction

Reaction Mechanism

1. The haloform is deprotonated by a strong base. 2. Generation of the dihalocarbene that reacts in situ with the olefin to generate a dihalocyclopropane. 3. The alkyllithium reacts with the dihalocyclopropane (metal-halogen exchange) followed by the loss of lithium halide to generate a cyclopropylidene, or carbenoid. 4. The cyclopropylidene rearranges to the corresponding allene.

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Doering-LaFlamme Reaction

Doering-LaFlamme Reaction

Reaction Mechanism

Learn More Named Reactions

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