30416-76-3

Upstream product

• 1449-46-3 benzyltriphenylphosphonium bromide 
• 98-88-4 benzoyl chloride 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 603-35-0 triphenylphosphine 
• 1484-50-0 desyl bromide 
• 618-32-6 Benzoyl bromide 
• 20767-31-1 benzyl(triphenyl)phosphonium bromide 
• 13246-50-9 benzylchlorotriphenylphosphorane 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 1530-47-8 (α-benzoyl-α-phenylmethylene)triphenylphosphonium bromide 

Downstream Products

• 501-65-5 diphenyl acetylene 
• 134-81-6 benzil 
• 791-28-6 Triphenylphosphine oxide 
• 1942-30-9 4-(phenylethynyl)nitrobenzene 
• 10423-78-6 (α-Benzoyl-4-nitrobenzyliden)triphenylphosphoran 
• 18054-69-8 C₂₈H₂₄N₂O₄S₂ 
• 105174-20-7 7-Methyl-3,3a-diphenyl-5-(toluene-4-sulfonyl)-5,5a-dihydro-3aH-benzo[c]isothiazolo[5,4-d]isothiazole 1,1-dioxide 
• 4110-33-2 2,4-dinitrobenzonitrile 
• 18365-29-2 triphenylphosphine oxide-nitric acid complex 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

Kinetics and mechanism of gas-phase pyrolysis of ylides. Part 3. 1 Thermal reactivity of α-carbonyl- and thiocarbonyl-stabilized methylenetriphenylphosphoranes

Fourteen ketone/thione-stabilized triphenylphosphonium methylides were subjected to conventional gas-phase and flash vacuum pyrolysis (FVP). The kinetics of the first-order thermal gas-phase reactions of all these compounds were investigated over 360-653K temperature range. The values of the Arrhenius logA and energy of activation of these ylides averaged 11.52±0.34s -1 and 133.20±3.14kJmol-1, respectively. The products of sealed-tube (static) and FVP were analyzed and compared. A mechanism is proposed to account for the products of reaction. The rate constants [k (s-1)] of the substrates at 500K were calculated and used to substantiate the proposed mechanism of pyrolysis, and to rationalize the thermal gas-phase reactivities of the ylides under study.

Solvent-free mechanochemical preparation of phosphonium salts, phosphorus ylides, and olefins

The present invention provides a method of preparing a phosphonium salt of the formula [R1R2R3P—CR4R5R6]X, comprising ball-milling a phosphine of the formula R1R2R3P with a compound of the formula XCR4R5R6; a method of preparing a phosphorus ylide of the formula R1R2R3P═CR4R5, comprising ball-milling a phosphonium salt of the formula [R1R2R3P—HCR4R5]X in the presence of a base; and a method of preparing an olefin of the formula R4R5C═CR7H or R4R5C═CR7R8, comprising ball-milling a phosphorus ylide of the formula R1R2R3P═CR4R5 with a compound of the formula R7C(O)H or R7C(O)R8. The inventive method produces phosphonium salts and phosphorus ylides by mechanical processing solid reagents under solvent-free conditions. The advantages of the present invention over conventional solution methods, include: (1) extremely high selectivity; (2) high yields; (3) low processing temperatures; (4) simple and scalable reactions using commercially available equipment; and (5) the complete elimination of solvents from the reaction.

Mechanically induced solid-state generation of phosphorus ylides and the solvent-free wittig reaction

We describe the nearly quantitative preparation of phosphorus ylides and the Wittig reaction occurring in the solid sate during high-energy mechanochemical processing. Initial insights into the details of the discovered chemical transformations indicate that high-energy mechanical processing supports the interaction of reacting centers by breaking crystallinity of the reactants and by providing mass transfer without a solvent. Copyright

Synthesis of C-glycosyl isoxazoles and branched-chain enuloses from 2,3-O-isopropylidene-D-glyceraldehyde

The synthesis of 5-glycosyl isoxazoles with 3-alkyl-, 3-aryl, 3,4-dialkyl, 3-aryl-4-alkyl or 3-alkyl-4-bromo substituents is reported. Deoxyenuloses were obtained from reaction of 2,3-O-isopropylidene-D-glyceraldehyde and several phosphorus ylides, which contain a carbonyl group, by a Wittig reaction. C-glycosyl α,β-unsaturated ketones were obtained, with the polyhydroxylate chain lengthened by two or three carbon atoms. In the second phase the ketones were transformed into the corresponding C-glycosyl α,β-unsaturated ketoximes, leading to the C-glycosyl isoxazoles, which were converted into the title compounds via removal of the isopropylidene group of suitably protected carbohydrates. The solubility of the synthetized C-glycosyl isoxazoles were modified by free hydroxyl groups in such a way that their behaviour against certain viruses and their potential antiviral activity could be studied.

CONVENIENT PREPARATION OF UNSYMMETRICALLY SUBSTITUTED BENZILS BY PERMANGANATE OXIDATION OF β-OXO PHOSPHORUS YLIDES

Oxidative cleavage of a range of ylides 4 with R1 and/or R2 being aromatic groups, using KMnO4 in a two-phase system, affords unsymmetrical benzils and 1-arylpropane-1,2-diones 5 in moderate to good yield, and the ylide formation and oxidation can be combined in a convenient one-pot method.Key words: Phosphorus ylides, oxidation, 1,2-diketones, benzils, permanganate, oxoalkylidenetriphenylphosphoranes.