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Date Posted: 05:21:40 01/22/16 Fri
Author: Rashed Ahmed
Subject: Doering–LaFlamme allene synthesis

In organic chemistry, the Doering–LaFlamme allene synthesis is a reaction of alkenes that converts them to allenes by insertion of a carbon atom.[1] This name reaction is named for William von Eggers Doering and a co-worker, who first reported it.[2]

Doering-LaFlamme Allene Synthesis.svg

The reaction is a two-stage process, in which first the alkene is reacted with dichlorocarbene or dibromocarbene to form a dihalocyclopropane. This intermediate is then reacted with a reducing metal, such as sodium or magnesium, or with an organolithium reagent. Either approach converts the dihalogenated carbon to a carbene or carbenoid-like structure. The resulting cyclopropylcarbene rearranges to form the allene product.[1] The electronic nature of the carbene intermediate is not entirely understood. Several different mechanisms for its electrocyclic rearrangement have been studied

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