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烷氧基苯和烷氧基萘在合成上重要的开环反应。

Synthetically important ring opening reactions by alkoxybenzenes and alkoxynaphthalenes.

作者信息

Talukdar Ranadeep

机构信息

Molecular Synthesis and Drug Discovery Laboratory, Centre of Biomedical Research, Sanjay Gandhi Postgraduate Institute of Medical Sciences Lucknow-226014 India

出版信息

RSC Adv. 2020 Aug 25;10(52):31363-31376. doi: 10.1039/d0ra05111j. eCollection 2020 Aug 21.

DOI:10.1039/d0ra05111j
PMID:35520658
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9056427/
Abstract

Alkoxybenzenes and alkoxynaphthalenes, as nucleophiles, have drawn great attention from organic chemists over the decades. Due to their high ring strain, those particular classes of molecules are often used in synthesis by utilizing their properties to undergo facile Friedel-Crafts alkylations. Different isomeric and low or densely substituted alkoxybenzenes are used for synthesis according to the structure of the target molecule. Isomeric methoxybenzenes, are the most commonly used molecule in this regard. This review aims to comprehensively cover the instances of different alkoxy-benzenes/naphthalenes used as nucleophiles for ring opening.

摘要

几十年来,作为亲核试剂的烷氧基苯和烷氧基萘一直备受有机化学家的关注。由于其高环张力,这些特定类型的分子常被用于合成,利用它们易于进行傅克烷基化反应的性质。根据目标分子的结构,使用不同的异构体以及低取代或高取代的烷氧基苯进行合成。在这方面,异构甲氧基苯是最常用的分子。本综述旨在全面涵盖不同烷氧基苯/萘用作亲核试剂进行开环反应的实例。

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Chem Sci. 2020 Feb 27;11(12):3146-3151. doi: 10.1039/d0sc00467g.
3
Ring-Opening Reactions of Donor-Acceptor Cyclobutanes with Electron-Rich Arenes, Thiols, and Selenols.给体-受体环丁烷与富电子芳烃、硫醇和硒醇的开环反应
Org Lett. 2019 Aug 16;21(16):6315-6319. doi: 10.1021/acs.orglett.9b02197. Epub 2019 Aug 5.
4
Ring-opening hydroarylation of monosubstituted cyclopropanes enabled by hexafluoroisopropanol.六氟异丙醇促进的单取代环丙烷的开环氢芳基化反应
Chem Sci. 2018 Jun 28;9(30):6411-6416. doi: 10.1039/c8sc02126k. eCollection 2018 Aug 14.
5
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6
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7
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8
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9
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10
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Beilstein J Org Chem. 2016 Dec 21;12:2816-2822. doi: 10.3762/bjoc.12.280. eCollection 2016.