Computational studies of Br ø nsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones

Abstract
The contribution to the energy barrier of a series of tethers in transannular cycloadditions of cycloalkenes with hydrazones has been computationally studied by using DFT. The Houk's distortion model has been employed to evaluate the influence of the tether in the cycloaddition reaction. That model has been extended to determine the contribution of each tether and, more importantly, the effect exerted between them. In addition to the distortion induced by the tethers, the entropy effects caused by them has also been studied. The analysis of the evolution of the electron localization function along the reaction revealed the highly concerted character of the reaction.

Beilstein J. Org. Chem. 2023, 19, 477–486. doi:10.3762/bjoc.19.37

Source: Beilstein Journal of Organic Chemistry - April 20, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: DFT distortion model hydrazones transannular cycloadditions Full Research Paper Source Type: research