95096-14-3

Upstream product

• 87269-11-2 N-benzoyl-N-isopropylhydroxylamine 
• 50632-53-6 N-isopropylhydroxylamine hydrochloride 
• 463962-26-7 thiobenzoyl 2-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinanyl)sulfide 
• 858220-30-1 N-isopropyl hydroxylamine hydrogen oxalate 
• 5080-22-8 N-isopropylhydroxyamine 
• 19172-47-5 Lawessons reagent 
• 98-88-4 benzoyl chloride 
• 95096-13-2 N-Acetoxy-N-isopropyl-benzamide 
• 157841-96-8 benzoyl 2-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinanyl)sulfide 
• 65-85-0 benzoic acid 
• 10364-94-0 1-benzoylimidazole 

Relevant academic research and scientific papers

Substituent effects on 15N NMR chemical shifts in selected N-alkylthiohydroxamic acids. A comparative study

The 15N NMR spectra of three N-alkyl-δ- carbomethoxyvalerothiohydroxamic acids (2) and six synthesized N-isopropylbenzothiohydroxamic acids (3) were measured and compared with appropriate spectra of structurally similar hydroxylamines (1), benz

Lawesson's reagent for direct thionation of hydroxamic acids: Substituent effects on LR reactivity

To explore the generality and scope of direct thionation of hydroxamic acids (HAs), the reaction of various structurally diverse HAs with Lawesson's reagent was investigated. The yield of thiohydroxamic acid (THAs) is poor when HAs possess bulky acyl and/or N-substituents, acidic α-hydrogen atoms, or an N-phenyl ring. THAs yields were correlated with Brown sigma parameter. The relative rates of two subsequent processes kT2 and kR2 were also measured. Correlation was also found for methine proton chemical shifts of N-isopropyl benzothiohydroxamic acids.

May dithiophosphoric acid participate in the set process?

Recently we have developed a convenient method for the synthesis of S-thioacyl dithiophosphates 1, excellent thioacylating reagents. When hydroxylamines with one bulky group or two substituents on the nitrogen atom are treated with S-thioacyl dithiophosph

S-Thioacyldithiophosphates in the synthesis of thiohydroxamic acids and O-thioacylhydroxylamines

S-Thioacyldithiophosphates proved to be excellent thioacylating agents. They are easily available from carboxylic acids. Due to their low reactivity towards oxygen nucleophiles and high reactivity towards nitrogen ones they found application in the synthe

Synthesis of S-thioacyl dithiophosphates, efficient and chemoselective thioacylating agents

Easily available acyl dithiophosphates are not stable and isomerise reversibly to O-thioacyl monothiophosphates, especially when subjected to heating. Much slower but probably irreversible isomerisation to S-thioacyl monothiophosphates occurs. Since equilibrium states are established and S-thioacyl (mono)thiophosphates form slowly, reaction mixtures contain generally both thioacylating and acylating agents, and consequently cannot be used for efficient thioacylation. On the other hand, treatment of a mixture of isomeric anhydrides with an excess of a dithiophosphoric acid leads to exclusive formation of S-thioacyl dithiophosphates. They appear to be excellent thioacylating agents: relatively stable, inert towards water and oxygen and therefore easy to handle. Reactions with nitrogen or sulfur nucleophiles proceed very rapidly under ambient conditions, yielding respective thioacyl derivatives. Isolation of the products is very simple. Due to the low reactivity of S-thioacyl dithiophosphates towards oxygen nucleophiles they can be used for direct thioacylation of multifunctional nucleophiles with unprotected hydroxy groups. Respective thioacyl derivatives cannot readily be obtained using other methods.

New, efficient and chemoselective method of thioacylation, starting from carboxylic acids

S-Acylation of dithiophosphoric acids yields mixed anhydrides 3; they readily isomerize to O-thioacyl 4 and S-thioacyl monothiophosphates 5, which treated with the excess of dithiophosphoric acid 2 can be easily converted into thioacyl dithiophosphates 6, excellent thioacylating reagents.

On the reaction of benzohydroxamic acids with Lawesson's Reagent

Reaction of Lawesson's Reagent (LR) with two N-alkyl benzohydroxamic acids is presented. In addition to the desired thiohydroxamic acids 2, the reduction process provides amides 3 and thioamides 4. An unexpectedly pronounced solvent effect on the course o