Carbanion Rearrangements
Carbanion rearrangements are a type of reaction in which a carbanion undergoes a rearrangement to attain more stability. These rearrangements can occur through various mechanisms, such as radical-pair dissociation-recombination or concerted mechanisms. Some common carbanion rearrangements include:
Wittig Rearrangements: These rearrangements can proceed as or rearrangements. The Wittig rearrangement proceeds via a radical-pair dissociation-recombination mechanism, while the Wittig rearrangement is a concerted mechanism.
Brook Rearrangement: This rearrangement is more common in organic synthesis due to Amos B. Smith’s anion relay chemistry (ARC). In this mechanism, a silyl group migrates towards the alcoholate, liberating another carbanion, which can subsequently participate in another nucleophilic attack. This allows multiple anion-dependent reactions to occur.
Benzilic Acid Rearrangement: This rearrangement involves a carbanionic 1,2-shift and is important in forming new carbon-carbon bonds and introducing functional groups.
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Carbanions
Carbanions, fundamental in organic chemistry, are negatively charged ions possessing a formal negative charge on a carbon atom. These reactive intermediates are essential in the synthesis of various organic compounds. Their unique properties, mechanisms of formation, and stability are key factors influencing their role in diverse reactions.
In this article, we will learn about, the definition, properties, formation methods, mechanisms, stability factors, and types of carbanions.
Table of Content
- What are Carbanions?
- Properties of Carbanions
- Formation of Carbanions
- Stability of Carbanions
- Types of Carbanions
- Reactions Involving Carbanions