Scribd
Upload
504 views5 pages

Favorskii Rearrangement

The Favorskii rearrangement involves treating α-halo ketones with a base and nucleophile, resulting in a skeletal rearrangement through a cyclopropanone intermediate to form carboxylic acids or their derivatives. Upon rearrangement, acyclic α-halo ketones form acyclic acid derivatives while cyclic substrates undergo ring contraction to form one-carbon smaller cyclic acids. The mechanism proceeds through deprotonation, ring closure to form a cyclopropenone intermediate, nucleophilic addition to the carbonyl, and cleavage of the CO-Cα bond to form a more stable carbanion product.

Uploaded by

Sabitry Yadav
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd
504 views5 pages

Favorskii Rearrangement

The Favorskii rearrangement involves treating α-halo ketones with a base and nucleophile, resulting in a skeletal rearrangement through a cyclopropanone intermediate to form carboxylic acids or their derivatives. Upon rearrangement, acyclic α-halo ketones form acyclic acid derivatives while cyclic substrates undergo ring contraction to form one-carbon smaller cyclic acids. The mechanism proceeds through deprotonation, ring closure to form a cyclopropenone intermediate, nucleophilic addition to the carbonyl, and cleavage of the CO-Cα bond to form a more stable carbanion product.

Uploaded by

Sabitry Yadav
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd
You are on page 1/ 5

Favorskii rearrangement

 Treatment of α-halo ketones possessing at least one α-hydrogen with base in the
presence of a nucleophile (alcohol, amine, or water) results in a skeletal
rearrangement via a cyclopropanone intermediate to give carboxylic acids or
carboxylic acid derivatives (esters or amides). This reaction is known as the Favorskii
rearrangement, and it is widely used for the synthesis of highly branched carboxylic
acids
 α-halo ketones when treated with a strong base (generally
alkoxides)  lead to the formation of esters with rearrangement of
the carbon frame work.
Mechanism
 The halogen substituent can be a chlorine, bromine or iodine, while the base is usually an alkoxide or
hydroxide. Upon rearrangement, acyclic α -halo ketones give acyclic carboxylic acid derivatives, while cyclic α
-halo ketone substrates undergo a ring-contraction reaction to afford one-carbon smaller cyclic carboxylic acid
derivatives.
 The rearrangement of unsymmetrical α -halo ketones leads to the product, which is formed through the
cleavage of the cyclopropanone intermediate to usually give the thermodynamically more stable of the two
possible carbanions.
 The base attacks the carbonyl carbon resulting in an anion which through phenyl migration forms the anion
of benzylic acid.
 Subsequent acidification can result in the acid itself.
 Initially, the α'-carbon is deprotonated to generate an enolate ion which is followed
by intra molecular nucleophilic substitution to give a cyclopropenone by ring
closure.
 Thus formed cyclopropenone undergoes nucleophilic addition by a base at the
carbonyl carbon which is followed by the cleavage of the CO-Cα bond. Usually the
cleavage occurs so as to give less substituted and more stable carbanion

You might also like