On a substituted benzene ring the position that bears the substituent is designated as the ipso position. This Perspective presents the history behind that designation.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.1c02128 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Transformative reactions in nitroarene chemistry: C-N bond cleavage, skeletal editing, and N-O bond utilization.
Org Biomol Chem
January 2025
Department of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo 162-0041, Japan.
Nitroarenes are highly versatile building blocks in organic synthesis, playing a pivotal role in various reactions. Common transformations involving nitroarenes include nucleophilic aromatic substitution (SAr) reactions, where the nitro group functions both as a potent electron-withdrawing group that activates the aromatic ring and as a leaving group facilitating the substitution. Additionally, the direct transformation of nitro groups, such as reduction-driven syntheses of amines and carboxylic acids, as well as -substitution SAr reactions, have been extensively explored.
View Article and Find Full Text PDFStabilizing Highly Reactive Aryl Carbanions in Water Microdroplets: Electrophilic -Substitution at the Air-Water Interface.
JACS Au
November 2024
Department of Chemistry, Indian Institute of Science Education and Research Tirupati, Tirupati 517507, India.
The fleeting existence of aryl carbanion intermediates in the bulk phase prevents their direct observation and spectroscopic measurement. In sharp contrast, we report the direct interception of such unstable species at the air-water interface of microdroplets. We observed the transformation of three types of aryl acids (benzoic, phenylsulfinic, and phenylboronic acids) into phenyl carbanion (Ph) in water microdroplets, as examined by mass spectrometry.
View Article and Find Full Text PDFSynthesis, Structure and Properties of Compounds Derived from Kotoite-related Structures: AMBO (A=Zn, Ba, Pb; B=Pb, Ba, Zn, Cu).
Chem Asian J
January 2025
Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, 560012, India.
A series of compounds with the general formula AMBO (A=Zn, Ba, Pb; B=Pb, Ba, Zn, Cu) related to the kotoite structure has been prepared employing high-temperature solid state methods. The substitution of transition elements in place of Zn ions resulted in colored compounds. The optical absorption spectra could be explained based on Tanabe-Sugano diagram and allowed d-d transitions.
View Article and Find Full Text PDFCu-Promoted -Hydroxylation of sp Bonds with Concomitant Aromatic 1,2-Rearrangement Involving a Cu-oxyl-hydroxo Species.
Inorg Chem
October 2024
Department of Chemistry, Carnegie Mellon University, Pittsburgh, Pennsylvania 15213, United States.
Herein, we report the first example of Cu-promoted β -hydroxylation of substituted benzophenones using a bidentate directing group (DG) and HO as an oxidant. In addition to the new C-O bond formed, the -oxidation induces a very unusual 1,2-rearrangement of the iminyl group to the vicinal γ position. This transformation is highly dependent on the substrate utilized (favored for 4-methoxy-substituted benzophenones) and on the DG used (2-picolylamine leads to selective γ-C-H functionalization, while β -oxidation requires 2-(2-aminoethyl)pyridine).
View Article and Find Full Text PDFOxidative Cleavage of Aromatic C-O Linkages by Oxoammonium Salts.
Chemistry
December 2024
Department of Chemistry, Zhejiang University, 866 Yuhangtang Rd, Hangzhou, 310058, China.
Oxidative cleavage of aromatic C(sp)-O bond is important to the conversion of biomass and plastic wastes into value-added chemicals. Here we put forward the oxidative cleavage of para-C-O bonds in phenolic compounds in use of oxoammonium salts as oxidant and water as the oxygen source. The mechanism is that oxoammonium cation activates water to form hydroxy-oxoammonium adduct and thus realizes the ipso-substitution of 4-alkoxyphenol, which is proved by substituent effect, isotope labelling experiments, and kinetic analysis.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!