Lactone trimer of dimethylketene

Clark, Raymond Donald

doi:10.1021/jo01288a031

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2007

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Insights into the Formation of Symmetrical Trimers of Dialkylated Ketenes Starting from Acid Chloride Precursors

Saaidi¹,

Doridot²,

Jeanneau³

et al. 2007

Monatsh. Chem.

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International audienceApplication of known dialkyl ketene di- and trimerization to more complex precursors could readily open the route to highly functionalized symmetrical cyclobuta-1,3-diones and cyclohexa-1,3,5-triones. We report herein the results on three substrates containing either a C=C double bond or a protected glycol moiety as illustrative functionalized groups. The nature of the substituents is found to be crucial: while cyclopentenyl and more constrained dioxolanocyclopentenyl precursors efficiently dimerize, a diallylic derivative fails. At the millimolar scale, methoxide-catalyzed trimerization shows limited reproducibility, even for the reported substrate tetramethylcyclobuta-1,3-dione. However, systematic studies, including the use of microwaves, demonstrate that formation of symmetrical trimers is favored under solvent-free conditions and conventional heating, which allowed us to isolate and characterize trispiro[4.1.4.1.4.1]octadeca-2,9,15-triene-6,12,18-trione

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Lactone trimer of dimethylketene

Cited by 4 publications

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Pure Liquids: Extended Data. Part 2 pp. 747

Pure Liquids: Extended Data. Part 2 pp. 747

2 Pure Liquids: References

Insights into the Formation of Symmetrical Trimers of Dialkylated Ketenes Starting from Acid Chloride Precursors

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