Büchner–Curtius–Schlotterbeck reaction

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The Büchner–Curtius–Schlotterbeck reaction is a chemical reaction that involves the conversion of ketones or aldehydes into α,β-unsaturated carbonyl compounds. This reaction is named after the chemists Eduard Büchner, Theodor Curtius, and Friedrich Schlotterbeck, who contributed to its development.

Mechanism

The Büchner–Curtius–Schlotterbeck reaction proceeds through a series of steps that typically involve the formation of an intermediate hydrazone or oxime, followed by a rearrangement and elimination process. The general mechanism can be summarized as follows:

1. Formation of a hydrazone or oxime from the ketone or aldehyde.
2. Rearrangement of the hydrazone or oxime to form an intermediate diazo compound.
3. Elimination of nitrogen gas (N₂) to yield the α,β-unsaturated carbonyl compound.

Applications

This reaction is particularly useful in organic synthesis for the preparation of α,β-unsaturated carbonyl compounds, which are valuable intermediates in the synthesis of various pharmaceuticals, natural products, and fine chemicals.

Related Reactions

The Büchner–Curtius–Schlotterbeck reaction is related to several other name reactions in organic chemistry, including:

• Wolff rearrangement
• Curtius rearrangement
• Beckmann rearrangement

See Also

• Ketone
• Aldehyde
• Hydrazone
• Oxime
• Diazo compound
• α,β-Unsaturated carbonyl compound