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Wittig Rearrangement

April 22, 2013

[1,2]-Wittig Rearrangement is a organic chemical reaction named after a German chemist Georg Wittig. This reaction is base-promoted reaction of ethers to yield secondary or tertiary alcohols. The reaction proceeds by [1,2] Rearrangement of an ether with an alkyllithium compound.

[1,2]-Wittig Rearrangement

The process of reaction and the migratory aptitude depends on the stability of the generated radicals. the reaction mechanism proceeds by free radical mechanism.

Mechanism of the reaction

  • Formation of free radicals when lithium atom migrates from carbon atom to oxygen atom.
  • Alkyl free radical combines with carbon free radical to form a rearranged product.
  • The rearranged product futher undergoes hydrolysis to form corresponding alcohol.

[1,2]-Wittig Rearrangement mechanism
For example, consider the following reaction

Examples

Predict the products for the forllowing reaction using [1,2]-Wittig Rearrangement.

[1,2]-Wittig Rearrangement examples

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