55236-56-1

Upstream product

• 4923-86-8 t-butyl(phenyl)phosphinic acid 
• 82220-43-7 tert-butylphenylphosphinic methanesulfonic anhydride 
• 62839-84-3 tert.-butyl-phenylthiophosphinic chloride 
• 98976-30-8 tert-Butylphenylphosphine oxide 
• 4923-85-7 tert-butylphenylphosphinic acid chloride 
• 82945-11-7 (R_p)-t-butyl(phenyl)phosphine oxide 
• 97730-09-1 trimethylsilyl tert-butylphenylphosphinate 
• 113680-14-1 tert-Butyl-phenylphosphinigsaeure-trimethylsilylester 
• 82220-41-5 tert-butylphenylphosphinic imidazolidide 
• 128175-77-9 (-)-S-t-butyl(phenyl)-S-trifluoromethyl phosphinothioate 
• 455-32-3 benzoyl fluoride 
• 55705-77-6 (S)-(-)-tert-butyl(phenyl)phosphinothioic acid 

Relevant academic research and scientific papers

New look into the synthesis of polyhalogenoarylphosphanes

The present study shows new aspects of the synthesis of polyhalogenoarylphosphanes. The sterically hindered anions Ph(R)P-Y- (1a-c, Y = O, lone pair; R = Ph, But) have been used to show the complexity of the reaction between phosphorus nucleophiles and hexahalogenobenzenes or 9-bromofluorene (E3). The Ph(But)P-O-(1a) anion reacts with hexachlorobenzene (E1), hexafluorobenzene (E2), or E3 to give Ph(R)P(O)X (4a-c, X = F, Cl, Br) with the release of the corresponding carbanion as a nucleofuge, followed by side reactions. In contrast, the lithium phosphides Ph(R)PLi (1b,c) react with hexahalogenobenzenes to give the corresponding diphosphanes 5a,b as the main product and traces of P-arylated products, i.e., Ph(R)P-C6X 5 (10a,b, X = Cl, F). Unexpectedly, Ph(But)PLi (1b) reacts with an excess of 9-bromofluorene to give only halogenophosphane Ph(Bu t)P-X. Taylor & Francis Group, LLC.

A facile conversion of thio- and selenophosphoric acids and their derivatives into fluoridates by means of reaction with silver fluoride

Treatment of numerous thio- or selenophosphorus acids with aqueous silver fluoride in CHCl3 at room temperature results in clean formation of the corresponding fluoridates. Analogous results were obtained with other phosphorothio (seleno)ates such as esters, amidates, or halides.

Fluorination of Trimethylsilyl Phosphites and their Structural Analogues by Sulfuryl Chloride Fluoride: Simple Preparation of Phosphorofluoridates and Related Compounds, including Deoxynucleoside Phosphorofluoridates

Trimethylsilyl esters of general formula RR'POSiMe3 react in a quantitative and fully chemoselective way with sulfuryl chloride fluoride, ClSO2F, under extremely mild conditions to give phosphorofluoridates RO(R'O)P(O)F of high purity.This work provides easy access to all type of fluoridates from non-toxic starting materials.The synthetic usefulness of this method is illustrated by the synthesis of 3'- and 5'-mononucleoside phosphorofluoridates 10 and 3',5'-dinucleoside phosphorofluoridates 11 from the corresponding nucleoside trimethylsilyl phosphites.

TRANSFORMATION OF ORGANOPHOSPHORUS S-TRIFLUOROMETHYLTHIOATES RR'P(O)SCF3 INTO FLUORIDES RR'P(O)F. STEREOCHEMICAL ASPECTS OF THIOCARBONYL FLUORIDE EXTRUSION

The stereochemical course of the thermal or by nucleophiles catalyzed extrusion reaction of thiocarbonyl fluoride from two diastereomeric (6) and optically active (10) organophosphorus S-trifluoromethylthioates has been investigated.To explain the observed retention of configuration at phosphorus in fluoridates 7 formed in the thermal reactions, a four center transition state for such reactions has been proposed.The lack of the stereoselectivity in the catalyzed reactions of 6, and the observed racemization of the final product 11 are briefly discussed.

CHEMISTRY OF S-TRIFLUOROMETHYL ORGANOPHOSPHOROTHIOATES AND THEIR STRUCTURAL ANALOGS A CONVENIENT SYNTHESIS OF ORGANOPHOSPHORUS FLUORIDATES

New organophosphorus compounds containing one or two different S-trifluoromethyl functionalities are synthesized in the reaction between the tri-coordinate phosphorus esters and bis-(trifluoromethane) disulfide.The catalytic effect exerted by the nucleoph

A NEW SYNTHESIS OF PHOSPHOROFLUORIDATES OF BIOLOGICAL INTEREST. THE REACTION OF PHOSPHOROAZOLIDES WITH BENZOYL FLUORIDE

Phosphoroazolides, including nucleoside derivatives, can be converted smoothly into the corresponding phosphorofluoridates by reaction with benzoyl fluoride.From these compounds oligonucleotides containing P-F instead of P-OH can be prepared.

Fluorination of Trimethylsilyl Phosphites and Their Structural Analogues by Sulphuryl Chloride Fluoride. A Facile Preparation of Phosphorofluoridates and Related Compounds

Trimethylsilyl esters of general formula RR'POSiMe3 react in a quantitative and fully chemoselective way with sulphuryl chloride fluoride to give phosphorofluoridates RR'P(O)F of high purity under extremely mild conditions.

Anhydrides of Phosphorus and Sulfur Acids, 2. Mixed Anhydrides of Phosphoric, Phosphonic, and Phosphinic Acids with Sulfonic Acids and Sulfuric Monoimidazolide. New Methods of Synthesis, Novel Structures, Phosphorylating Properties

New applications of methods leading to anhydrides RR'P(O)OSO2R'' (1) are described: a) Reaction of acids RR'P(O)OH (2) with sulfonic imidazolides. b) Reaction of phosphorus imidazolides 4 with sulfonic acids and sulfonic anhydrides.New methods of synthesis of anhydrides 1 have been developed. c) Reaction of phosphorus acid silyl esters RR'P(O)OSiMe3 (9) with methanesulfonic and trifluoromethanesulfonic anhydrides. d) Reaction of bis(trimethylsilyl) tert-butylphosphonate (10) with methanesulfonic acid leading to tBuP(O)(OSO2Me)2 (11). e) Reaction of stannyl phosphate (EtO)2P(O)OSnMe3 (15) with methanesulfonic anhydride. f) Reaction of phosphorus acid silyl esters 9 with trimethylsilyl trifluoromethanesulfonate.All methods result in high yields and can be adapted to a variety of anhydrides 1 derived from phosphoric, phosphonic, and phosphinic acids on the one hand and methanesulfonic, trifluoromethanesulfonic acids and sulfuric monoimidazolide on the other.Phosphonium intermediates have been demonstrated by low temperature FT 31P NMR spectroscopy for reaction b) and c).The anhydrides 1 are readily converted into imidazolides 4 by the reaction with N-(trimethylsilyl)imidazole which proceeds via two distinct phosphonium intermediates.With neutral and weakly basic nucleophiles, the anhydrides 1 behave as phosphorylating agents.