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

Jorge Escorihuela, Wilhelmus J.E. Looijen, Xiao Wang, Adelia J.A. Aquino, Hans Lischka, Han Zuilhof

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
JournalJournal of Organic Chemistry
DOIs
StateAccepted/In press - 2020

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