153595-69-8

Basic information

• Product Name: N-(triphenyl-λ5-phosphanylidene)thiophene-2-carboxamide
• Synonyms: N-(triphenyl-λ5-phosphanylidene)thiophene-2-carboxamide
• CAS NO: 153595-69-8
• Molecular Weight: 387.442
• Mol File: 153595-69-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-(triphenyl-λ5-phosphanylidene)thiophene-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(triphenyl-λ5-phosphanylidene)thiophene-2-carboxamide(153595-69-8)
• EPA Substance Registry System: N-(triphenyl-λ5-phosphanylidene)thiophene-2-carboxamide(153595-69-8)

Safety Data

• Hazardous Substances Data: 153595-69-8(Hazardous Substances Data)

Upstream product

• 5271-67-0 2-Thiophenecarbonyl chloride 
• 603-35-0 triphenylphosphine 
• 2046-39-1 2-thiophenecarbonyl azide 
• 1400655-60-8 (thiophen-2-yl)formamido 2,2-dimethylpropanoate 
• 1373758-55-4 3-(thiophen-2-yl)-1,4,2-dioxazole-5-one 
• 17698-15-6 N-hydroxythiophene-2-carboxamide 

Downstream Products

• 1003-31-2 thiophene-2-carbonitrile 

Relevant articles and documents

Interweaving Visible-Light and Iron Catalysis for Nitrene Formation and Transformation with Dioxazolones

Herein, visible-light-driven iron-catalyzed nitrene transfer reactions with dioxazolones for intermolecular C(sp3)-N, N=S, and N=P bond formation are described. These reactions occur with exogenous-ligand-free process and feature satisfactory to excellent yields (up to 99 %), an ample substrate scope (109 examples) under mild reaction conditions. In contrast to intramolecular C?H amidations strategies, an intermolecular regioselective C?H amidation via visible-light-induced nitrene transfer reactions is devised. Mechanistic studies indicate that the reaction proceeds via a radical pathway. Computational studies show that the decarboxylation of dioxazolone depends on the conversion of ground sextet state dioxazolone-bounding iron species to quartet spin state via visible-light irradiation.

Unprecedented Transformation of a Directing Group Generated in Situ and Its Application in the One-Pot Synthesis of 2-Alkenyl Benzonitriles

An unprecedented protocol for the transformation of benzoyl azides into benzonitrile derivatives via iminophosphoranes generated in situ is described. The strategy was successfully applied to the de-novo synthesis of 2-alkenylated benzonitrile derivatives from benzoyl azides through ortho CH activation/alkenylation followed by subsequent rearrangement. The salient features of this protocol involve incorporation of two important functionalities through cyanation and olefination in one pot under mild reaction conditions by using a less expensive Ru catalyst. The mechanism was established by isolating and characterising (using 31PNMR) an intermediate with two ortho functionalities, iminophosphorane and olefin, under specific reaction conditions. Directly functional! Cyanation and olefination was accomplished in one pot from benzoyl azides through an unprecedented directing group transformation. The method generates benzonitriles and can be used for the synthesis of 2-alkenylated benzonitrile derivatives (see scheme).