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

doi:10.1021/acs.joc.0c01674

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^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

10 Citations (Scopus)

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 language	English
Pages (from-to)	13557–13566
Journal	Journal of Organic Chemistry
Volume	85
Issue number	21
DOIs	https://doi.org/10.1021/acs.joc.0c01674
Publication status	Published - 26 Oct 2020

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@article{02444874bc944dcca5e71782b1c52512,

title = "Cycloaddition of Strained Cyclic Alkenes and Ortho-Quinones: A Distortion/Interaction Analysis",

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. ",

author = "Jorge Escorihuela and Looijen, {Wilhelmus J.E.} and Xiao Wang and Aquino, {Adelia J.A.} and Hans Lischka and Han Zuilhof",

year = "2020",

month = oct,

day = "26",

doi = "10.1021/acs.joc.0c01674",

language = "English",

volume = "85",

pages = "13557–13566",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "21",

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TY - JOUR

T1 - Cycloaddition of Strained Cyclic Alkenes and Ortho-Quinones

T2 - A Distortion/Interaction Analysis

AU - Escorihuela, Jorge

AU - Looijen, Wilhelmus J.E.

AU - Wang, Xiao

AU - Aquino, Adelia J.A.

AU - Lischka, Hans

AU - Zuilhof, Han

PY - 2020/10/26

Y1 - 2020/10/26

N2 - 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.

AB - 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.

U2 - 10.1021/acs.joc.0c01674

DO - 10.1021/acs.joc.0c01674

M3 - Article

AN - SCOPUS:85095818084

SN - 0022-3263

VL - 85

SP - 13557

EP - 13566

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

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

Abstract

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