Cycloaddition of Strained Cyclic Alkenes and Ortho-Quinones: A Distortion/Interaction Analysis
NAGIOS: RODERIC FUNCIONANDO

Cycloaddition of Strained Cyclic Alkenes and Ortho-Quinones: A Distortion/Interaction Analysis

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Cycloaddition of Strained Cyclic Alkenes and Ortho-Quinones: A Distortion/Interaction Analysis

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Escorihuela Fuentes, Jorge; Looijen, Wilhelmus J. E.; Wang, Xiao; Aquino, Adelia J. A.; Lischka, Hans; Zuilhof, Han
This document is a artículoDate2020
The chemistry of strained unsaturated cyclic compounds has experienced remarkable growth in recent years via the development of metal−free click reactions. Among these reactions, the cycloaddition of cyclopropenes and their analogues to ortho-quinones has been established as a highly promising click reaction. The present work investigates the mechanism involved in the cycloaddition of strained dienes to ortho-quinones and structural factors that would influence this reaction. For this purpose, we use B97D density functional theory calculations throughout, and for relevant cases, we use spin component−scaled MP2 calculations and single−point domain-based local pair natural orbital coupled cluster (DLPNO-CCSD(T)) calculations. The outcomes are analyzed in detail using the distortion/interaction model, and suggestions for future experimental work are made.

    Escorihuela Fuentes, Jorge Looijen, Wilhelmus J. E. Wang, Xiao Aquino, Adelia J. A. Lischka, Hans Zuilhof, Han 2020 Cycloaddition of Strained Cyclic Alkenes and Ortho-Quinones: A Distortion/Interaction Analysis Journal of Organic Chemistry 85 21 13557 13566
https://doi.org/10.1021/acs.joc.0c01674

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