The photochemical cyclization of butadiene to cyclobutene is used to illustrate certain problems connected with the application of the Woodward-Hoffmann rules to photoinduced concerted reactions. Energy levels for the ground states and excited states of butadiene, cyclobutene, and a large number of intermediate configurations have been calculated, thus enabling the establishment of potential surfaces, from which probable reaction paths for the thermal and photoinduced reactions can be determined. It appears that the thermal disrotatory process is improbable since this would require an activation energy of ca. 100 kcal/mole. Further, it turns out that the driving force for the photoinduced ring closure as a disrotatory process derives from a favorable symmetric excited state, whereas Woodward and Hoffmann consider an antisymmetric excited state.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.