Inter- and Intramolecular Cycloaddition Reactions of Ethenetricarboxylates with Styrenes and Halostyrenes

Abstract

Inter- and intramolecular cycloaddition reactions of ethenetricarboxylates with styrenes and α-halostyrenes have been investigated. The reactions of ethenetricarboxylates with styrenes or α-bromostyrenes in the presence of SnCl₄ or SnBr₄ stereoselectively gave 2,4-cis-substituted cyclobutanes. The intramolecular cycloaddition reactions of a series of styrene-functionalized ethenetricarboxylate amides, including in situ generated derivatives, showed high diversity of reaction modes depending on the structures and substituents of the substrates. The regioselectivity and stereoselectivity of the reactions as well as reaction mechanisms were discussed based on the DFT calculations.

Key words

cyclobutane - ethenetricarboxylate - styrene - intermolecular cycloaddition - intramolecular cycloaddition

Publikationsverlauf

Eingereicht: 25. August 2020

Angenommen nach Revision: 24. September 2020

Artikel online veröffentlicht:
02. November 2020

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