Chemistry

Electrocyclic reaction and its 3D visualization

Electrocyclic reaction and its 3D visualization



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Literature example [1] by Niwayama: Interplay between theory and experiment: Reversal of the torque selectivity of the electrocyclic ring opening by a Lewis acid

Niwayama has performed calculations on the torque selectivity of the thermal ring-opening reaction of 3-acetylcyclobutene II and verified the theoretical results through experiments. The thermolysis of 3-acetylcyclobutene results in a mixture of E.- and Z-Serve with a slight preference for that E.- Serve. Lewis acids can be used to reduce this preference in favor of the Z- Reverse your service.

Information on the literature reaction [1]:

Title:
Interplay between theory and experiment: reversal of the torquoselectivity of the electrocyclic ring opening reaction of 3-acetylcyclobutene by a Lewis acid
Abstract:
The rotational selectivity of the thermal ring opening of the title component II, which can be synthesized from the commercially available 1,1-cyclobutanedicarboxylic acid I, can be predicted by ab initio calculations. It can be demonstrated through experiments that the Lewis acidZnI.2 the slight preference for thatE.-Dien III to the thermodynamically less stableZ-The IV reverses.
Literature:
Niwayama, S. (1996):Interplay of Theory and Experiment: Reversal of the Torquoselectivity of the Electrocyclic Ring Opening of 3-Acetylcyclobutene (II) by a LewisAcid.. In: J. Org. Chem.. 61(2), 640-646


Video: Electrocyclic Reactions. Organic Chemistry Lessons (August 2022).