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Isotope effects for Lewis acid catalyzed Diels-Alder reactions. The experimental transition state

✍ Scribed by Daniel A. Singleton; Steven R. Merrigan; Brett R. Beno; K.N. Houk

Book ID
104261931
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
289 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

2H and 13C kinetic isotope effects were determined for all positions on isoprene in its reactions with methyl vinyl ketone, ethyl acrylate, and acrolein catalyzed by Et2AICI. The results are taken as supporting a highly asynchronous concerted [4+2] cycloaddition. Comparison of the experimental isotope effects with calculated values supports this conclusion and the accuracy of the calculated transition structure.

📜 SIMILAR VOLUMES

On the mechanism of Diels—Alder reaction
On the mechanism of Diels—Alder reactions catalyzed by Lewis acids
✍ 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.

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## Catechol boron bromide (I) andferrocenium hexqpuorophosphate (2) function as Lewis acid catalysts for the Dick-Alder reaction. The development of chiral Lewis acids as catalysts for the asymmetric induction of Diels-Alder and other reactions is a subject of current interest. Recent years have s