Generation of nitrene by the photolysis of N-substituted iminodibenzothiophene.

J Org Chem

Department of Material Systems Engineering and Life Science, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan.

Published: September 2008

To evaluate the ability of dibenzothiophene N-substituted sulfilimines as photochemical nitrene sources, their photolyses in the presence of several trapping reagents, such as sulfides, olefins, and phosphorus compounds, were performed. In the reactions, the corresponding imino-transfer compounds, namely sulfilimines, aziridines, and iminophosphoranes, were formed in good yields, indicating dibenzothiophene N-tosyl and N-acylsulfilimines have a potent nature as nitrogen sources.

Download full-text PDF

Source
http://dx.doi.org/10.1021/jo800604tDOI Listing

Publication Analysis

Top Keywords

generation nitrene
4
nitrene photolysis
4
photolysis n-substituted
4
n-substituted iminodibenzothiophene
4
iminodibenzothiophene evaluate
4
evaluate ability
4
ability dibenzothiophene
4
dibenzothiophene n-substituted
4
n-substituted sulfilimines
4
sulfilimines photochemical
4

Similar Publications

Reactivity of Anomalous Aziridines for Versatile Access to High Fsp Amine Chemical Space.

Acc Chem Res

January 2025

Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, Wisconsin 53706, United States.

ConspectusThe manipulation of strained rings is a powerful strategy for accessing the valuable chemical frameworks present in natural products and active pharmaceutical ingredients. Aziridines, the smallest N-containing heterocycles, have long served as building blocks for constructing more complex amine-containing scaffolds. Traditionally, the reactivity of typical aziridines has been focused on ring-opening by nucleophiles or the formation of 1,3-dipoles.

View Article and Find Full Text PDF

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 PDF

Copper and Silver Trispyrazolylborate-Phosphinoazide Complexes: Synthesis, Characterization, and Nitrene Generation.

Inorg Chem

January 2025

Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva, 21007 Huelva, Spain.

Phosphinoazide complexes of the composition TpM-L (M = Cu, Ag, and L = 2-azido-1,3-bis(2,6-diisopropylphenyl)-2,3-dihydro-1-1,3,2-diazaphosphole) have been synthesized and structurally characterized. Their thermal decomposition led to cyclodiphosphazenes as a result of the metal-mediated coupling of two nitrene units in a process that takes place in both a stoichiometric and catalytic manner. Experimental data have allowed proposing a mechanistic pathway for this new transformation.

View Article and Find Full Text PDF

Photoredox/Iron Dual-Catalysis-Enabled [4 + 2] Cyclization of Acyl Nitrene with Alkynes.

Org Lett

December 2024

College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, China.

In this work, the annulation of acyl nitrene with alkynes is reported under photoredox/iron dual-catalysis for the synthesis of a series of isoquninalin-2-ones. The reaction is featured with a high reaction regioselectivity and good reaction generality. In particular, the resulting isoquinalin-2-ones could be structurally elaborated into several biologically interesting scaffolds.

View Article and Find Full Text PDF

An azine-based, non-palindromic, neutral NNN-pincer ligand was synthesised in a single step with an yield of 85%. The palladation of the ligand, using Pd(OAc), was performed in acetonitrile at room temperature to obtain the pincer complex in 88% yield through a simple, cost-effective, and straightforward synthetic procedure. The structure of the complex was confirmed by H NMR, C NMR, FT-IR, and mass spectrometry.

View Article and Find Full Text PDF

Want 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!