Synthesis of Bispyrrolidines by Radical Cyclisation of Diallylamines Using Phosphorus Hydrides

Parsons, Andrew F.; Wright, Anthony

doi:10.1055/s-2008-1072789

Cited by 12 publications

(3 citation statements)

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“…Parson and Wright designed a nice reaction sequence for the reaction of phosphinic acid or phosphinothionic acid with diallylamines. The initial radical generated reacted with a diallylamine to form intermediate 381 which underwent second radical reaction with another diallylamine to afford bispyrrolidines 382 264. The Montchamp group also demonstrated that hydrophosphonyl radical can add to the same carbon of alkyne twice to form 1,1-bis-H-phosphinate 383.Scheme 162A limited literature information was found on the reactions of alkyl-or arylphosphonyl radicals [(RO)RP(O)•].…”

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confidence: 97%

Recent advances in sulfur- and phosphorous-centered radical reactions for the formation of S–C and P–C bonds

et al. 2015

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mentioning

confidence: 97%

Recent advances in sulfur- and phosphorous-centered radical reactions for the formation of S–C and P–C bonds

et al. 2015

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“…The phosphorus‐centered radical [HPO 2 − ]• was detected in these studies. There is much work presenting reactions, in which hypophosphites, including sodium hypophosphite, act as a radical‐chain carrier . There are also data indicating that the first coating layer on the substrates having aluminum or iron appears via the exchange reaction :

\begin{matrix} true \\ right Fe + {Ni}^{2 +} \to {Fe}^{2 +} + Ni \end{matrix}

\begin{matrix} true \\ right {2 Al + 3 Ni}^{2 +} \to {2 Al}^{3 +} + 3 Ni \end{matrix}

…”

Section: Literature Hypotheses Of the Ni‐p Coating Deposition Mechanismmentioning

confidence: 99%

Summary of Existing Models of the Ni‐P Coating Electroless Deposition Process

Stankiewicz

Szczygieł

2013

Int J of Chemical Kinetics

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Electroless nickel‐phosphorous plating is a technique often employed in preparation of protective, decorative, and functional coatings. Several feasible mechanisms are discussed in the literature. The influence of process parameters on metal coating deposition is analyzed and described. Nevertheless, some basics of the process and the fundamental aspects of plating still not explained. A number of research groups make an effort to provide a description of the process with a physical model. The aim is to design a theoretical model that could be valid under operating conditions on a practical scale. This work gives a short review of the published data on the mechanism and kinetics of the electroless Ni‐P deposition process. The review also touches a novel approach—proposition to analyze data using artificial intelligence tools.

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“…Their highly efficient addition reactions to alkenes have been achieved with transition metal catalysts [22][23][24]. A radical reaction involving phosphorus-centered radicals generated in situ is a classical method for P-C bond formation [25][26][27][28][29][30]; however, the use of primary phosphines and phosphine oxides in a radical reaction is relatively rare compared to that of secondary phosphines and phosphine oxides [31][32][33][34][35][36][37][38]. The stereochemistry on a phosphorus atom has not received much attention, despite the fact that the introduction of at least three different substituents to the phosphorus atom gives rise to the stereogenic center on the phosphorus atom.…”

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confidence: 99%

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

et al. 2021

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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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Synthesis of Bispyrrolidines by Radical Cyclisation of Diallylamines Using Phosphorus Hydrides

Abstract: Sequential radical addition-cyclisation reactions of diallylamines using either hypophosphorous acid or a bisphosphinothioate are shown to afford bispyrrolidines in good to excellent yields.

Cited by 12 publications

References 3 publications

Recent advances in sulfur- and phosphorous-centered radical reactions for the formation of S–C and P–C bonds

Recent advances in sulfur- and phosphorous-centered radical reactions for the formation of S–C and P–C bonds

Summary of Existing Models of the Ni‐P Coating Electroless Deposition Process

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

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