Mechanistic study on the intramolecular oxa-[4 + 2] cycloaddition of substituted o-divinylbenzenes

  • XingHui ZhangEmail author
Original Paper


This paper reports a detailed computational study of the mechanisms of formation of oxacyclic derivatives from substituted o-divinylbenzenes by a photoinduced intramolecular oxa-[4 + 2] cycloaddition. The reaction mechanism and chemoselectivity of trans, trans- and cis, trans-substituted ortho-divinylbenzene were studied. Detailed density functional theory calculations show that the reaction system proceeds through two main steps: light-active intramolecular cyclization and Diels-Alder reactions of C=O. Trans, trans-products of cycloaddition of substituted o-divinylbenzenes are more favored than cis, trans-products. Compared with different substituents, the cycloaddition reaction of phenyl ketone has a relatively low activation barrier, and the strong electron-withdrawing group on the benzene ring is more favorable for the intramolecular cycloaddition reaction of substituted o-divinylbenzenes.


Cycloaddition Substituted o-divinylbenzenes Photoinduced Density functional theory 



This work was supported by the Natural Science Foundation of Department of Education, Gansu Province (2016B-121). We are grateful to the Gansu Province Supercomputer Center for essential support. We are grateful to the reviewers for their invaluable suggestions.


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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.College of Chemical EngineeringLanzhou University of Arts and ScienceLanzhouChina

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