Aziridinyl phosphine oxides derived from the radical addition of perfluoroheptyl iodide to diethyl vinylphosphonate

1969 ◽  
Vol 14 (3) ◽  
pp. 403-405
Author(s):  
Jerry P. Moreau ◽  
Leon H. Chance
Keyword(s):  
Radical Addition ◽  
Phosphine Oxides ◽  
Diethyl Vinylphosphonate

Regioselective radical arylation: silver-mediated synthesis of 3-phosphorylated coumarins, quinolin-2(1H)-one and benzophosphole oxides

2019 ◽  
Vol 17 (35) ◽  
pp. 8175-8184 ◽  
Author(s):  
Hong Hou ◽  
Yue Xu ◽  
Haibo Yang ◽  
Chaoguo Yan ◽  
Yaocheng Shi ◽  
...  
Keyword(s):  
Radical Addition ◽  
Cyclization Reaction ◽  
Phosphine Oxides ◽  
Radical Arylation ◽  
Propynoic Acid

A silver-mediated domino radical addition/cyclization reaction of diaryl- or dialkyl-phosphine oxides with propynoic acid derivatives delivering 3-phosphorylated coumarins, quinolin-2(1H)-one and benzophosphole oxides is presented.

TBAI-catalyzed oxidative C–H functionalization: a new route to benzo[b]phosphole oxides

2016 ◽  
Vol 52 (13) ◽  
pp. 2815-2818 ◽  
Author(s):  
Yun Zhang ◽  
Gaobo Hu ◽  
Dumei Ma ◽  
Pengxiang Xu ◽  
Yuxing Gao ◽  
...  
Keyword(s):  
Radical Addition ◽  
Phosphine Oxides ◽  
Metal Free ◽  
One Step

The first metal-free, efficient TBAI-catalyzed radical addition/cyclization of diaryl(arylethynyl)phosphine oxides with toluene derivatives has been developed, affording a general, one-step approach to structurally sophisticated benzo[b]phosphole oxides via sequential C–H functionalization along with the formation of two new C–C bonds.

scholarly journals Primary Phosphines and Phosphine Oxides with a Stereogenic Carbon Center Adjacent to the Phosphorus Atom: Synthesis and Anti-Markovnikov Radical Addition to Alkenes

Organics ◽  
2021 ◽  
Vol 2 (4) ◽  
pp. 395-403
Author(s):  
Toshiaki Murai ◽  
Ryota Wada ◽  
Kouji Iwata ◽  
Yuuki Maekawa ◽  
Kazuma Kuwabara ◽  
...  
Keyword(s):  
Carbon Atom ◽  
Phosphorus Atom ◽  
Organophosphorus Compounds ◽  
Radical Addition ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Reaction Conditions ◽  
High Yields ◽  
Oxidized Products

Organophosphorus compounds with stereogenic phosphorus and carbon atoms have received increasing attention. In this regards, primary phosphines with a stereogenic carbon atom adjacent to the phosphorus atom were synthesized by the reduction in phosphonates and phosphonoselenoates with a binaphthyl group. Their oxidized products, i.e., phosphine oxides with a stereogenic tetrasubstituted carbon atom, were found to undergo BEt3-mediated radical addition to cyclohexene to give P-stereogenic secondary phosphine oxides with a diastereoselectivity of 91:9. The products were characterized by ordinary analytical methods, such as Fourier transform infrared spectroscopy; 1H, 13C, and 31P NMR spectroscopies; and mass spectroscopy. Computational studies on the phosphorus-centered radical species and the obtained product implied that the thermodynamically stable radical and the adduct may be formed as a major diastereomer. The radical addition to a range of alkenes took place in an anti-Markovnikov fashion to give P-stereogenic secondary phosphine oxides. A variety of functional groups in the alkenes were tolerated under the reaction conditions to afford secondary phosphine oxides in moderate yields. Primary phosphines with an alkenyl group, which were generated in situ, underwent intramolecular cyclization to give five- and six-membered cyclic phosphines in high yields after protection by BH3.

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