The “cobra effect” in the imidazolinone series: how a donor can disable the nucleophilicity-Reference-Cited by-同舟云学术

登录注册会员服务联系我们

The “cobra effect” in the imidazolinone series: how a donor can disable the nucleophilicity

Published:2023 Issue:18 Volume:10 Page:4550-4558
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Gazizov A. S.¹^ORCID,Kuznetsova E. A.¹²,Kamaletdinov A. Z.¹²,Smolobochkin A. V.¹^ORCID,Lodochnikova O. A.¹,Gerasimova D. P.¹^ORCID,Burilov A. R.¹,Pudovik M. A.¹

Affiliation:

1. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science, Arbuzova str., 8, Kazan 420088, Russian Federation

2. Kazan National Research Technological University, 420015, K. Marksa str. 68, Kazan, Russian Federation

Abstract

Contrary to chemical intuition, electron-donating groups decrease the nucleophilicity of the double bond in imidazolin-2-ones, switching their reactivity from “enamide” to “base”. Enamide reactivity can be recovered by a careful choice of the catalyst and solvent.

Funder

Russian Science Foundation

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/QO/D3QO00580A

Reference57 articles.

1. A survey of Hammett substituent constants and resonance and field parameters

2. Reactivity scales for quantifying polar organic reactivity: the benzhydrylium methodology

3. Asymmetric Enamine Catalysis

4. Enamine Catalysis Is a Powerful Strategy for the Catalytic Generation and Use of Carbanion Equivalents

5. Structure–Nucleophilicity Relationships for Enamines

同舟云学术

1.学者识别学者识别

2.学术分析学术分析

3.人才评估人才评估

"同舟云学术"是以全球学者为主线，采集、加工和组织学术论文而形成的新型学术文献查询和分析系统，可以对全球学者进行文献检索和人才价值评估。用户可以通过关注某些学科领域的顶尖人物而持续追踪该领域的学科进展和研究前沿。经过近期的数据扩容，当前同舟云学术共收录了国内外主流学术期刊6万余种，收集的期刊论文及会议论文总量共计约1.5亿篇，并以每天添加12000余篇中外论文的速度递增。我们也可以为用户提供个性化、定制化的学者数据。欢迎来电咨询！咨询电话：010-8811{复制后删除}0370

www.globalauthorid.com

TOP