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Paterno-Buchi Reaction

Paterno-Buchi reaction   Named Reactions in Organic Synthesis

Reaction category:
Pericyclic and photochemical reactions

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Other featured photochemical reaction:

In 1909 the Italian chemist Emanuele Paternò di Sessa reported an interesting reaction between benzaldehyde and 2-methyl-2- butene on exposure to sunlight. Two isomeric compounds were isolated from the reaction that were characterized as trimethylene oxides or oxetanes. During 1954 the Swiss chemist George Hermann Büchi decided to re-examine this earlier work and identify the exact structure of the products. Subsequently the photochemical cycloaddition between aldehydes and alkenes to form oxetanes became known as the Paterno-Büchi reaction. During the reaction the carbonyl substrate, which can be either an aldehyde or ketone, absorbs energy and adds across the carbon-carbon double bond of the alkene.

The reaction is useful synthetically as it is highly region- and stereoselective and has subsequently been used in several total synthesis campaigns. For example during the first total synthesis of the cytotoxic agent (±)- euplotin A the correct stereochemistry of the required dihydrofuran substrate was established via the Paterno-Büchi reaction between ethyl glyoxylate and furan. (Reference: Total synthesis of the cytotoxin (±)- euplotin A. J. Am. Chem.Soc. 2001, 123, 9455-9456)


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Other reaction categories:

Electrophilic aromatic substitution

Nucleophilic substitution reactions

Heterocycle-formation

Transition metal-catalyzed couplings

Oxidation

Reactions involving carbonyl compounds

Reduction reactions

Rearrangement reactions

Electrophilic addition reactions


Some relevant Alfa Aesar products for the Paterno-Buchi reaction:

Benzaldehyde, 99+%
Benzaldehyde, 98%
2-Methyl-2-butene, tech. 90%, remainder mainly 2-methyl-1-butene
Ethyl glyoxylate, ca 50% soln. in toluene
Furan, 99%, stab. with ca 250ppm BHT

We have many aldehydes and ketones in our portfolio.

 

 

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