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Lewis acid-induced rearrangement of the Diels–Alder dimer of tetrachlorocyclopentadienone: structure reassignments

✍ Scribed by Philip E Eaton; Datong Tang; Richard Gilardi


Book ID
104232128
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
69 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


The structures of various perhalodiones available by isomerization of the Diels-Alder dimers of tetrachloro-and tetrabromocyclopentadienone have finally been determined unambiguously.


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On the Diels–Alder reactions and the Lew
✍ Paul A. Clarke; Rebecca L. Davie; Simon Peace 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 76 KB

C5 position by a vinyl group were found to undergo competing tandem sigmatropic rearrangement/Diels-Alder cyclisation when heated under standard Diels-Alder cyclisation conditions. This rearrangement became the exclusive pathway when the reactions were performed in the presence of a Lewis acid.

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✍ V. Branchadell; A. Oliva; J. Bertran 📂 Article 📅 1985 🏛 Elsevier Science 🌐 English ⚖ 261 KB

The effect of Lewis acid catalysts on the mechanism of Diels-Alder reactions is studied using the MINDO/3 method. It is found that they tend to increase the two-step character of the process through a more important participation of the charge-transfer configuration.