Triphenylphosphine oxide-catalyzed stereoselective poly- and dibromination of unsaturated compounds

2014 ◽  
Vol 50 (58) ◽  
pp. 7817 ◽  
Author(s):  
Tian-Yang Yu ◽  
Yao Wang ◽  
Xiu-Qin Hu ◽  
Peng-Fei Xu
Keyword(s):  
Triphenylphosphine Oxide ◽  
Unsaturated Compounds

ChemInform Abstract: Triphenylphosphine Oxide-Catalyzed Stereoselective Poly- and Dibromination of Unsaturated Compounds.

ChemInform ◽  
2014 ◽  
Vol 45 (51) ◽  
pp. no-no
Author(s):  
Tian-Yang Yu ◽  
Yao Wang ◽  
Xiu-Qin Hu ◽  
Peng-Fei Xu
Keyword(s):  
Triphenylphosphine Oxide ◽  
Unsaturated Compounds

Xenon Trioxide Adducts of O-Donor Ligands; [(CH3)2CO]3XeO3, [(CH3)2SO]3(XeO3)2, (C5H5NO)3(XeO3)2, and [(C6H5)3PO]2XeO3

2018 ◽  
Author(s):  
Katherine Marczenko ◽  
James Goettel ◽  
Gary Schrobilgen
Keyword(s):  
Room Temperature ◽  
Triphenylphosphine Oxide ◽  
Donor Ligands ◽  
Mechanical Shock ◽  
X Ray Diffraction ◽  
X Ray ◽  
Oxygen Coordination ◽  
Xenon Trioxide ◽  
Distorted Octahedra ◽  
Coordination Spheres

Oxygen coordination to the Xe(VI) atom of XeO<sub>3</sub> was observed in its adducts with triphenylphosphine oxide, dimethylsulfoxide, pyridine-N-oxide, and acetone. The crystalline adducts were characterized by low-temperature, single-crystal X-ray diffraction and Raman spectroscopy. Unlike solid XeO<sub>3</sub>, which detonates when mechanically or thermally shocked, the solid [(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>PO]<sub>2</sub>XeO<sub>3</sub>, [(CH<sub>3</sub>)<sub>2</sub>SO]<sub>3</sub>(XeO<sub>3</sub>)<sub>2</sub>,<sub> </sub>and (C<sub>5</sub>H<sub>5</sub>NO)<sub>3</sub>(XeO<sub>3</sub>)<sub>2</sub> adducts are insensitive to mechanical shock, but undergo rapid deflagration when ignited by a flame. Both [(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>PO]<sub>2</sub>XeO<sub>3 </sub>and (C<sub>5</sub>H<sub>5</sub>NO)<sub>3</sub>(XeO<sub>3</sub>)<sub>2</sub> are air-stable whereas [(CH<sub>3</sub>)<sub>2</sub>SO]<sub>3</sub>(XeO<sub>3</sub>)<sub>2</sub> slowly decomposes over several days and [(CH<sub>3</sub>)<sub>2</sub>CO]<sub>3</sub>XeO<sub>3</sub> undergoes adduct dissociation at room temperature. The xenon coordination sphere of [(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>PO]<sub>2</sub>XeO<sub>3</sub> is a distorted square pyramid which provides the first example of a five-coordinate XeO<sub>3</sub> adduct. The xenon coordination spheres of the remaining adducts are distorted octahedra comprised of three Xe---O secondary contacts that are approximately trans to the primary Xe–O bonds of XeO<sub>3</sub>. Quantum-chemical calculations were used to assess the Xe---O adduct bonds, which are predominantly electrostatic σ-hole bonds between the nucleophilic oxygen atoms of the bases and the σ-holes of the xenon atoms.

Polymer-Bound Triphenylphosphine and 4,4′-Dinitroazobenzene as a Coupling Reagents for Chromatography-Free Esterification Reaction

2019 ◽  
Vol 16 (7) ◽  
pp. 1024-1031
Author(s):  
Diparjun Das ◽  
Kalyani Rajkumari ◽  
Lalthazuala Rokhum
Keyword(s):  
Microwave Irradiation ◽  
Solid Phase ◽  
Reaction System ◽  
Triphenylphosphine Oxide ◽  
High Yield ◽  
Sustainable Chemistry ◽  
Esterification Reaction ◽  
Coupling Reagent ◽  
Simple Filtration ◽  
Esterification Reactions

Aim and Objective: Sustainable production of fine chemicals both in industries and pharmaceuticals heavily depends on the application of solid-phase synthesis route coupled with microwave technologies due to their environmentally benign nature. In this report, a microwave-assisted esterification reaction using polymer-bound triphenylphosphine and 4,4′-dinitroazobenzene reagent system was investigated. Materials and Methods: The solvents were obtained from Merck India. Polymer-bound triphenylphosphine (~3 mmol triphenylphosphine moiety/g) was acquired from Sigma-Aldrich. The progress of the reaction was observed by thin-layer chromatography. All the reactions were performed in Milestones StartSYNTH microwave. The NMR spectra were recorded on Bruker Avance III 300, 400, and 500 MHz FT NMR Spectrometers. Using azo compound and polymer-bound triphenyl phosphine as a coupling reagent, esterification of different carboxylic acids with alcohols was performed under microwave irradiation. Results: Esterification of benzoic acid with 1-propanol under microwave irradiation gave a high yield of 92% propyl benzoate in 60 minutes only. Isolation of the ester products was relatively simple as both the byproducts polymer-bound triphenylphosphine oxide and hydrazine could be removed by simple filtration. The rates of reactions were found to be directly proportional to the pKa of the benzoic acids. Conclusion: 4,4′-Dinitroazobenzene was introduced as a novel coupling reagent, in conjugation with polymer-bound triphenylphosphine, for esterification reactions under microwave irradiation. The low moisture sensitivity of the reaction system, easy separation of the byproducts, and column chromatographyfree isolation of esters help our methods with application significance, particularly from the ‘Sustainable Chemistry’ perspective.

Sila-, bora-, thio-, and phosphono-carboxylation of unsaturated compounds with carbon dioxide: An overview

2021 ◽  
Vol 48 ◽  
pp. 101522
Author(s):  
Shi Nan ◽  
Wang Hai-Bin ◽  
Gao Li ◽  
Zhang Jing-Yao ◽  
Guo Jian-Feng ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Unsaturated Compounds

scholarly journals THE CATALYTIC EFFECT OF FERRICYANIDE IN THE OXIDATION OF UNSATURATED COMPOUNDS BY OXYGEN

1931 ◽  
Vol 94 (2) ◽  
pp. 411-413
Author(s):  
G. Payling Wright ◽  
James B. Conant ◽  
S.E. Kamerling
Keyword(s):  
Catalytic Effect ◽  
Unsaturated Compounds
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