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Cyclobutenones: The synthesis and Diels Alder reactivity of 4,4-dimethylcyclobutenone

✍ Scribed by T.Ross Kelly; Robert W. McNutt

Publisher
Elsevier Science
Year
1975
Tongue
French
Weight
206 KB
Volume
16
Category
Article
ISSN
0040-4039

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✦ Synopsis

In conjunction with another project it recently became necessary to develop a synthon which would be synthetically equivalent to terelactone (U1 but more reactive than 1 as a dienophile in the Diels Alder reaction.

4,4-Dimethylcyclobutenone (2) appeared to be an attractive candidate since it seemed that the relief of angle strain' resulting from the rehybridisation of the olefinic carbons

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Synthesis and Diels-Alder Reactivity of
Synthesis and Diels-Alder Reactivity of 2,3,5,6-Tetramethylidenenorbornane
✍ Olivier Pilet; Pierre Vogel πŸ“‚ Article πŸ“… 1981 πŸ› John Wiley and Sons 🌐 German βš– 519 KB

Pd-catalyzed double carbomethoxylation of the Diels-A lder adduct of cyclopentadiene and maleic anhydride yielded the methyl norbornane-2,3-endo-5,6-exotetracarboxylate (4) which was transformed in three steps into 2,3,5,6-tetramethyIidenenorbornane (1). The cycloaddition of tetracyanoethylene (TCNE