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Main Menu. 17.5 The Wittig and Related Reactions. The Wittig Reaction (formation of alkenes). General Reaction:. R´ and R” can be H or alkyl group. Phosphine oxide. Wittig reagent (a phosphonium ylide ). General Reaction:. base. Formation of Wittig Reagents. A phosphonium salt.

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17 5 the wittig and related reactions

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17.5 The Wittig and Related Reactions

The Wittig Reaction

(formation of alkenes)

General Reaction:

R´ and R” can be H or alkyl group.

Phosphine oxide

Wittig reagent (a phosphoniumylide)

Formation of wittig reagents

General Reaction:


Formation of Wittig Reagents

A phosphonium salt

Ph: phenyl

  • The alkyl halides need to have at least one H.


Potassium tert-butoxide

Mechanism of wittig reaction

Mechanism of Wittig Reaction



Examples of wittig reaction

Examples of Wittig Reaction



Wittig reagents favor the Z (cis) isomer.

Reactions of aldehydes and ketones with horner emmons reagent

Horner-Emmons reaction (general reaction):

Reactions of Aldehydes and Ketones with Horner-Emmons Reagent

R = Et (most common)

Phosphate diester

Horner-Emmons reagent

Formation of horner emmons reagent

Arbuzov (Perkow) reaction:

Formation of Horner-Emmons Reagent


Stabilized carboanion

R = alkyl, acyl or R’OC(O)-

Mechanism of horner emmons reaction

Mechanism of Horner-Emmons Reaction



Water insoluble

Water soluble

Examples of horner emmons reaction

Examples of Horner-Emmons Reaction

> 99%

Horner-Emmons reagents favor the E (trans) isomer.

Learning check

1. What could be the reagent for the following transformation?

Learning Check

2. What should be the product from the following reaction?

Learning check1

Main Menu transformation?

3. What could be the product for the following reaction?

Learning Check