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Cycloaddition reactions of o-quinone methides with polarized olefins

Vitaly Aleksandrovich Osyanin 1
Vitaly Aleksandrovich Osyanin
, 
Anton Vladimirovich Lukashenko 1
Anton Vladimirovich Lukashenko
, 
Dmitry Vladimirovich Osipov 1
Dmitry Vladimirovich Osipov
1 Samara State Technical University
10.1070/RCR4971
Published 30 November 2020
Review , RCR4971, Volume 90, Issue 3, 324-373
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Osyanin V. A., Lukashenko A. V., Osipov D. V. Cycloaddition reactions of o-quinone methides with polarized olefins // Russian Chemical Reviews. 2020. Vol. 90. No. 3. pp. 324-373.
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Osyanin V. A., Lukashenko A. V., Osipov D. V. Cycloaddition reactions of o-quinone methides with polarized olefins // Russian Chemical Reviews. 2020. Vol. 90. No. 3. pp. 324-373.
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TY - JOUR
DO - 10.1070/RCR4971
UR - https://rcr.colab.ws/publications/10.1070/RCR4971
TI - Cycloaddition reactions of o-quinone methides with polarized olefins
T2 - Russian Chemical Reviews
AU - Osyanin, Vitaly Aleksandrovich
AU - Lukashenko, Anton Vladimirovich
AU - Osipov, Dmitry Vladimirovich
PY - 2020
DA - 2020/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 324-373
IS - 3
VL - 90
ER -
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@article{2020_Osyanin,
author = {Vitaly Aleksandrovich Osyanin and Anton Vladimirovich Lukashenko and Dmitry Vladimirovich Osipov},
title = {Cycloaddition reactions of o-quinone methides with polarized olefins},
journal = {Russian Chemical Reviews},
year = {2020},
volume = {90},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4971},
number = {3},
pages = {324--373},
doi = {10.1070/RCR4971}
}
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Osyanin, Vitaly Aleksandrovich, et al. “Cycloaddition reactions of o-quinone methides with polarized olefins.” Russian Chemical Reviews, vol. 90, no. 3, Nov. 2020, pp. 324-373. https://rcr.colab.ws/publications/10.1070/RCR4971.
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Keywords

o-quinone methides
Diels-Alder reaction
electrophilic
hydroxyphenyl substituted p-quinone methides
nucleophilic
oligomerization
push-pull and captodative olefins

Abstract

The review summarizes and systematizes the [4+2]-cycloaddition reactions of \emph{o}-quinone methides with electron-rich and electron-deficient olefins. The electron-rich substrates include vinyl ethers, vinyl sulfides, enamines, enamides, enols, furans, benzofurans and indoles, while the electron-deficient substrates are esters of unsaturated carboxylic acids, vinyl azides and quinones. Reactions with push-pull and captodative olefins are also considered. The mechanisms of some reactions are presented. A separate part of the review addresses reactions of p-quinone methides containing an o-hydroxyphenyl substituent at the exocyclic carbon atom, which can isomerize to o-quinone methides. Much attention is paid to oligomerization of \emph{o}-quinone methides, which proceeds in the absence of active dienophiles or nucleophiles.

The bibliography includes 217 references.

Funders

Russian Foundation for Basic Research
19-13-50441

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