Aza-Wittig Reaction: Mechanism | Examples

The reaction of aza-ylides ( also called as iminophosphoranes) with different carbonyl molecules is called the
aza-Wittig reaction. In this post described the Aza-Wittig Reaction Mechanism with Examples.

Aza-Wittig Reaction Mechanism

Mechanism of Aza-Wittig Reaction are defined in two steps as follow

First step : the PPh₃ reacts with an alkyl-azide and generate an iminophosphorane by loosing of nitrogen N₂ (also called Staudinger reaction).

Second step: the nucleophilic nitrogen of the iminophosphorane attacks the carbonyl group and four-membered intermediate (oxazaphosphetane) generate, from oxazaphosphetane product Schiff base and the by-product triphenylphosphine oxide are released. this is the Aza-Wittig Reaction Mechanism

Aza-Wittig Reaction Examples:

Aza-Wittig Reaction with Mechanism and Examples has been shown below

Related Reactions:

1. Wittig Reaction
2. Staudinger Reaction

References:

1. Catalytic Wittig and aza-Wittig reactions ^
2. Strategic Applications of Named Reactions in Organic Synthesis ^^
3. Aza-Wittig Reaction: Mechanism | Examples