3096-04-6Relevant articles and documents
Microemulsions as reaction media. Self-organizing assemblies in an environmental cleanup problem
Menger, F. M.,Park, H.
, p. 176 - 180 (1994)
A microemulsion system has been developed that simultaneously destroys three environmental contaminants by combined oxidative/hydrolytic pathways.The method is rapid, cheap, and mild.No special equipment (stirrer, heater, photolyser, etc.) is required.Self-organization converts a seemingly intractable 8-component mixture into a useful system, a tactic discovered by living cells long ago.
An Alternative Metal-Free Aerobic Oxidative Cross-Dehydrogenative Coupling of Sulfonyl Hydrazides with Secondary Phosphine Oxides
Cheng, Feixiang,Liu, Jianjun,Liu, Teng,Yu, Rong,Zhang, Yanqiong
, p. 253 - 262 (2019/12/28)
An alternative metal-free, efficient and practical approach for the preparation of phosphinothioates is established via the aerobic oxidative cross-dehydrogenative coupling (CDC) of sulfonyl hydrazides with secondary phosphine oxides catalyzed by tetrabutylammonium iodide (TBAI) in the presence of atmospheric oxygen. The strategy provides an array of diverse phosphinothioates in good to excellent yields. Furthermore, two representative bioactive molecules are synthesized on up to gram scale by utilizing this method.
A Robust Methodology for the Synthesis of Phosphorothioates, Phosphinothioates and Phosphonothioates
Jones, David J.,O'Leary, Eileen M.,O'Sullivan, Timothy P.
supporting information, (2020/03/27)
A robust methodology for the synthesis of phosphorothioates, phosphinothioates and phosphonothioates, including those bearing low molecular weight S-alkyl side-chains, is presented. Application of the “caesium effect” in conjunction with the disulfide 3,3’-dithiobis(propionitrile), which acts as a shelf-stable sulfur source, avoids recourse to malodorous alkanethiols and toxic P?Cl precursors. A diverse range of sulfur-containing organophosphorus targets, including phosphorus-based heterocycles, may be prepared in consistently high yields. This chemistry also provides ready access to the corresponding DBU salts which are potential substrates for Pd-catalysed coupling reactions. (Figure presented.).
Solvent-free preparation method of alkylthiophosphonate
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Paragraph 0029-0035, (2019/03/06)
The invention discloses a solvent-free preparation method of an alkylthiophosphonate. The method comprises the following steps: 1) mixing an alcohol compound, a sulfur powder and a pH reagent, and reacting under the action of Bronsted acid at a temperatur
NHC-Catalyzed Metathesis and Phosphorylation Reactions of Disulfides: Development and Mechanistic Insights
Crocker, Reece D.,Hussein, Mohanad A.,Ho, Junming,Nguyen, Thanh V.
supporting information, p. 6259 - 6263 (2017/05/12)
The development of efficient methods for the metathesis and phosphorylation reactions of disulfide compounds is of widespread interest due to their important synthetic utility in polymer, biological, medicinal and agricultural chemistry. Herein, we demonstrate the use of N-heterocyclic carbenes (NHCs) as versatile organocatalysts to promote these challenging reactions under mild conditions. This metal- and oxidant-free protocol is operationally simple with very short reaction times. The interplay between the nucleophilicity and basicity of NHCs in these reactions were also elucidated by NMR studies and high-level ab initio calculations.
A NEW, UNEXPECTED REACTION OF PHOSPHONOCHLORIDOTHIONATES WITH ALKYL ARYL ETHERS AND ALKYL CHLORIDES UNDER THE FRIEDEL-CRAFTS REACTION CONDITIONS
Omelanczuk, Jan
, p. 93 - 102 (2007/10/02)
Phosphonochloridothionates have been found to react in the presence of Lewis acids with alkyl aryl ethers to give S-alkyl O-aryl phosphonothiolates and with alkyl halides to form products of the S-alkylation. Key words: Alkyl arel ethers; phosphonochloridothionates; alkylation; S-alkyl O-aryl phosphonothiolates; S-alkyl alkyl(aryl) dichlorophosphonium salts; conductivity.
PHOSPHORORGANISCHE VERBINDUNGEN 90 Methodische Ausgestaltung der P-C und P-S-Cyanolyse am Beispiel einiger Heterophosphoniumsalze
Horner, Leopold,Jordan, Manfred
, p. 215 - 220 (2007/10/02)
Treatment of allylamido-phosphonium salts with dry tetrabutylammonium cyanide in methylenechloride delivers after removal of the allyl group phosphinous acid amides with retention of configuration (P-C-cyanolysis).Allyl-O-alkylphosphonium salts undergo the Arbosov reaction under the above conditions, while allyl-S-alkyl phosphonium salts undergo fission of the P-S bond (P-S cyanolysis).Equally good results were obtained using KCN in methylene chloride accompained by catalytic amounts of 18-crown-6 ether; thus optically active benzyl-methyl-phenyl-phosphine-sulfid gave the corresponding phosphine with retention of configuration.Dithiophosphinic acid esters and thiophosphinic acid amides, after conversion to the corresponding quasiphosphonium salts via S-alkylation and subsequent treatment with tetrabutylammonium cyanide in methylenechloride, also give the corresponding thiophosphinous acid ester and phosphinous acid amide respectively.Thiophosphinic acid O-alkyl esters (R2P(S)OR') give however the thiophosphinic S-alkyl ester (R2P(O)SR') via an Arbusov reaction.The P-C cyanolysis of allyl-triphenylphosphoniumbromide using KCN/18-crown-6 or tetrabutylammonium cyanide in aprotic medium stops at the stage of the intermediary red-coloured ylide; addition of a proton-donor then results in the subsequent rearrangement to the corresponding propenyl-phosphonium salt.
