Formaldehyde

Sandra Forbes

Product Manager

Formaldehyde can undergo oxidation or reduction processes with relative ease.

Nonetheless, its use ought to be abstained from because of its carcinogenic properties. Metal hydrides serve as more appropriate reducing agents.

Name Reactions

Cannizzaro Reaction

The redox disproportionation of non-enolizable aldehydes into carboxylic acids and alcohols is carried out in a concentrated base environment.

α-Keto aldehydes undergo intramolecular disproportionation to yield the product in high yields.

Mechanism of the Cannizzaro Reaction

An intriguing variation known as the Crossed Cannizzaro Reaction employs formaldehyde as the reducing agent:

Currently, a wide range of oxidizing and reducing agents can be utilized to achieve such conversions with higher yields, rendering the Cannizzaro Reaction of limited synthetic significance today, except for the aforementioned transformation of α-keto aldehydes.

When aldehydes are treated under basic conditions, it is prudent to consider the Cannizzaro Reaction as a potential source of side products.

Recent Literature

Lithium Bromide: A Versatile, Gentle, and Reusable Reagent for Performing Solvent-Free Cannizzaro, Tishchenko, and Meerwein-Ponndorf-Verley Reactions

M. M. Mojtahedi, E. Akbarzadeh, R. Sharifi, M. S. Abaee, Org. Lett., 2007, 9, 2791-2793.

DOI: 10.1021/ol070894t

An Extremely Effective and Enantioselective Intramolecular Cannizzaro Reaction Catalyzed by TOX/Cu(II)

P. Wang, W.-J. Tao, X.-L. Sun, S. Liao, Y. Tang, J. Am. Chem. Soc., 2013, 135, 16849-16852.

DOI: 10.1021/ja409859x

Synthesis of 3-Substituted Phthalides from 2-Formylarylketones via Nucleophile- or Light-Triggered Reactions

D. C. Gerbino, D. Augner, N. Slavoy, H.-G. Schmalz, Org. Lett., 2012, 14, 2338-2341.

DOI: 10.1021/ol300757m

A One-Pot Tandem Oxidation-Cannizzaro Reaction of Aryl Methyl Ketones Facilitated by Ytterbium Triflate

M. Curini, F. Epifano, S. Genovese, M. C. Marcotullio, O. Rosati, Org. Lett., 2005, 7, 1331-1333.

DOI: 10.1021/ol050125e

Quoted from: https://www.organic-chemistry.org/chemicals/reductions/formaldehyde.shtm & https://www.organic-chemistry.org/namedreactions/cannizzaro-reaction.shtm

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