3096-03-5Relevant academic research and scientific papers
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 00222-0028, (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
Acid/Phosphide-Induced Radical Route to Alkyl and Alkenyl Sulfides and Phosphonothioates from Sodium Arylsulfinates in Water
Lin, Ya-Mei,Lu, Guo-Ping,Wang, Gui-Xiang,Yi, Wen-Bin
, p. 382 - 389 (2017/04/26)
A newly developed aqueous system with acid and phosphide was introduced in which odorless and stable sodium arylsulfinates can in situ generate arylsulfenyl radicals. These radicals have high reactivity to react with alkynes, alkenes, and H-phosphine oxides for the synthesis of alkyl and alkenyl sulfides and phosphonothioates. The control experiments and quantum calculations are also performed to gain insights into the generation mechanism of arylsulfenyl radicals. Notably, the chemistry is free of thiol odors, organic solvents, and metals.
Metal- and base-free reductive coupling reaction of P(O)-H with aryl/alkyl sulfonyl chlorides: a novel protocol for the construction of P-S-C bonds
Wang, Dungai,Zhao, Jinlong,Xu, Weigang,Shao, Changwei,Shi, Zheng,Li, Liang,Zhang, Xinghua
supporting information, p. 545 - 549 (2017/01/25)
Novel and efficient synthesis of S-aryl/alkyl phosphinothioates from P(O)-H and aryl/alkyl sulfonyl chlorides under metal- and base-free conditions is described. This reaction provides an alternative strategy for the construction of P-S-C bonds in moderate to excellent yields. Moreover, this method can be readily applied to gram-scale preparation.
Catalyst- and oxidant-free coupling of disulfides with H-phosphine oxide: construction of P–S bond leading to thiophosphinates
Xia, Minfang,Cheng, Jiang
supporting information, p. 4702 - 4704 (2016/10/03)
An efficient protocol for the synthesis of thiophosphinates is presented, involving direct coupling of P–S bond between disulfides and H-phosphine oxide in moderate to good yields with good functional group compatibility. This procedure shows some advanta
N-(diphenylphosphinothioyl)hydroxylamine: Preparation, characterisation and base-induced transposition of sulfur and oxygen atoms in its O-benzoyl derivative
Harger, Martin J. P.
, p. 3205 - 3209 (2007/10/03)
N-(Diphenylphosphinothioyl)hydroxylamine 5 has been prepared from Ph2P(S)Cl using H2NOSiMe3 and has been converted into its O-benzoyl derivative Ph2P(S)NHOCOPh 6. The principal reaction of the derivative 6 with base (NaOMe or ButNH2) is rearrangement, transposition of sulfur and oxygen giving Ph2P(O)NHSCOPh 7; this then reacts further, forming the phosphinic amide Ph2P(O)NH2 together with PhCO2Me or PhCONHBut. The rearrangement probably involves intramolecular nucleophilic displacement of benzoate by the P=S group of 6, forming an intermediate with P, N and S atoms in a three-membered ring.
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.
PHASE-TRANSFER CATALYTIC ALKYLATION OF HYDROTHIOPHOSPHORYL COMPOUNDS. IV. REACTIONS WITH PRIMARY ALKYL HALIDES
Aladzheva, I. M.,Odinets, I. L.,Petrovskii, P. V.,Mastryukova, T. A.,Kabachnik, M. I.
, p. 431 - 437 (2007/10/02)
A convenient general method for the synthesis of compounds containing a thiophosphoryl group was elaborated on the basis of the Michaelis-Becker reaction with the use of the method of phase-transfer catalysis. The influence of the nature of the hydrothiophosphoryl compounds, of the alkylating agents, and of the reaction conditions on the yields of alkylated products was investigated in detail.
THE REACTIONS OF α-ALKOXYALLYLPHOSPHINE OXIDE YLIDES WITH SILICON, SULPHUR AND PHOSPHORUS ELECTROPHILES
Devchand, Dipak K.,Murray, Alistair W.,Smeaton, Elizabeth
, p. 4635 - 4638 (2007/10/02)
Anions (2), derived from α-methoxyallylphosphine oxides (1), react with silicon, sulphur and phosphorus electrophiles in a highly regioselective fashion to give the products of γ-attack.
