CIDNP as a tool to unveil the reaction mechanism: interaction of mixed phosphonium–iodonium ylide with<i>p</i>-methoxyphenylacetylene

Левина, И. И.; Tarasov, V. F.; Podrugina, T. A.; Nekipelova, T. D.

doi:10.1039/c9ra05697a

Cited by 4 publications

(5 citation statements)

References 20 publications

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“…531 This investigation yielded interesting information about the mechanism of the reaction between the two compounds. 531 Next, a more recent class of applications that primarily target photo-CIDNP as a source of nuclear spin hyperpolarization and sensitivity enhancement in liquids is illustrated below via a number of representative examples. Table 3 summarizes the current status of photo-CDNP nuclear hyperpolarization in solution, whereas photo-CIDNP in solids falls into a different mechanistic category addressed separately in section 3.8.…”

Section: Chemicalmentioning

confidence: 94%

“…530 Another application involved 31 P photo-CIDNP to study the interaction between phosphonium-iodonium ylide and pmethoxyphenylacetylene. 531 This investigation yielded interesting information about the mechanism of the reaction between the two compounds. 531 Next, a more recent class of applications that primarily target photo-CIDNP as a source of nuclear spin hyperpolarization and sensitivity enhancement in liquids is illustrated below via a number of representative examples.…”

Section: Chemicalmentioning

confidence: 94%

“…14-fold sensitivity enhancement, and enabling 19 F MRI of this compound . Another application involved 31 P photo-CIDNP to study the interaction between phosphonium-iodonium ylide and p -methoxyphenylacetylene . This investigation yielded interesting information about the mechanism of the reaction between the two compounds …”

Section: Hyperpolarization Techniquesmentioning

confidence: 99%

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Spin Hyperpolarization in Modern Magnetic Resonance

et al. 2023

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Magnetic resonance techniques are successfully utilized in a broad range of scientific disciplines and in various practical applications, with medical magnetic resonance imaging being the most widely known example. Currently, both fundamental and applied magnetic resonance are enjoying a major boost owing to the rapidly developing field of spin hyperpolarization. Hyperpolarization techniques are able to enhance signal intensities in magnetic resonance by several orders of magnitude, and thus to largely overcome its major disadvantage of relatively low sensitivity. This provides new impetus for existing applications of magnetic resonance and opens the gates to exciting new possibilities. In this review, we provide a unified picture of the many methods and techniques that fall under the umbrella term "hyperpolarization" but are currently seldom perceived as integral parts of the same field. Specifically, before delving into the individual techniques, we provide a detailed analysis of the underlying principles of spin hyperpolarization. We attempt to uncover and classify the origins of hyperpolarization, to establish its sources and the specific mechanisms that enable the flow of polarization from a source to the target spins. We then give a more detailed analysis of individual hyperpolarization techniques: the mechanisms by which they work, fundamental and technical requirements, characteristic applications, unresolved issues, and possible future directions. We are seeing a continuous growth of activity in the field of spin hyperpolarization, and we expect the field to flourish as new and improved hyperpolarization techniques are implemented. Some key areas for development are in prolonging polarization lifetimes, making hyperpolarization techniques more generally applicable to chemical/biological systems, reducing the technical and equipment requirements, and creating more efficient excitation and detection schemes. We hope this review will facilitate the sharing of knowledge between subfields within the broad topic of hyperpolarization, to help overcome existing challenges in magnetic resonance and enable novel applications.

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Section: Chemicalmentioning

confidence: 94%

Section: Chemicalmentioning

confidence: 94%

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Spin Hyperpolarization in Modern Magnetic Resonance

et al. 2023

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“…Függetlenül Fotokatalizátor A reakció kis hatékonysága, a körülmények változtatására közel binárisan viselkedő rendszer, valamint a kutatócsoportban vizsgált katalitikus folyamatok érzékenysége [315] [40,43,47] Mindemellett kutatásunkkal egyidőben Suero és munkatársai demonstrálták a pszeudociklusos diazo-jodónium ilidek alkalmazhatóságát aril-diazoalkánok szintézisére, [52] így a 354 vegyület felhasználására irányuló további kísérleteinket felfüggesztettük. 62%-os hozamban (9. táblázat).…”

Section: Grafikon: Fotokatalizátorok Hatékonysága (Kalibrált Gc-fid H...unclassified

“…19 F NMR (282 MHz, CDCl3) δ -69,80 (d, J = 8,4 Hz). 13 C NMR (75 MHz, CDCl3) δ 144 , 8, 134,0,133,9, 132,3, 128,4, 128,1, 127,7, 127,4, 126,7 (q, J = 287,8 Hz),126,4,125,8,125,6,125,2,124,6,123,3,115,4,59,0, 58,9 (q, J = 25,6 Hz),43,1, 36,9. IR (ATR, cm -1 ) 3063, 2952, 2884, 2864, 2807, 2252, 1592, 1571, 1456, 1337, 1279, 1251, 1231, 1207, 1158, 1099, 1049, 1028, 900, 856, 791, 774, 749, 604, 508, 445, 427.…”

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confidence: 99%

Trikoordinált jódvegyületek előállításainak és alkalmazásainak fejlesztése

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Köszönetnyilvánítás Mindenekelőtt köszönöm szüleimnek, testvéremnek és családomnak azt a végtelen szeretetet és gondoskodást, mellyel szüntelenül körülvettek doktori munkám során. Köszönöm páromnak, Englert Dóra Fanninak, hogy szeretetével és kitartásával támogatott ezen dolgozat megírása alatt. Hálás köszönettel tartozom témavezetőmnek, Dr. Novák Zoltánnak, hogy tudásával, párját ritkító türelmével, magas színvonalú munkakörnyezet megteremtésével, valamint a hazai és nemzetközi konferenciákon való révételeim biztosításával támogatta szakmai előmenetelemet. Köszönettel tartozom a "régi" Novák csoport tagjainak, hogy kezdő doktoranduszként befogadva, szakmai támogatással és hatalmas segítséggel támogattak. Külön szeretném megköszönni dr. Gonda Zsombornak, dr. Mészáros Ádámnak és dr. Tóth Balázsnak, hogy laboratóriumi munkám során elviseltek, valamint szakmai segítségükön túl baráti pártfogásukkal is egyengették utam. Köszönöm az "új" csoporttagoknak, közülük is kiemelve Varga Bálintnak, Adamik Rékának és Adamis Bálintnak, hogy jó kedélyükkel tették könnyebbé a mindennapi munkát. Makó Zitának és Szabó Csabának köszönöm az ipari kutatási témák megvalósítására nyújtott segítségüket.

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Radicals in Annulation of Mixed Benzoyl Phosphonium‐Iodonium Ylide and Acetylenes Explored by EPR‐ST Spectroscopy

Potapov,

Levina,

Motyakin

et al. 2024

Asian J Org Chem

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Annulation of mixed phosponium‐iodonium ylides and compounds with a triple bond is an interesting example of the synthesis of different types of heterocycles in one‐pot, metal‐free systems at ambient temperature to give substituted oxazoles in the reaction with nitriles and phosphorus‐containing λ5‐phosphinolines and substituted furans in the reaction with acetylenes. The iodonium group in the mixed ylides provides the possibility for the radical initiation of the reaction. Herein, we investigated the generation of primary radicals and the formation of phosphorus‐containing products in the photolysis of benzoyl phosphonium‐iodonium ylide alone and in its reaction with acetylenes in DCM by EPR and 31P NMR spectroscopies with the use of two most popular spin traps, PBN and DMPO. The results allowed us to account the crucial difference in the registered radicals in the two systems for the aggregation of the components, with ylide molecules forming a core and acetylene molecules being a shell of the aggregates in DCM, in which the annulation occurs. The peculiarities of the reactions of PBN and DMPO with generated radicals are discussed.

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CIDNP as a tool to unveil the reaction mechanism: interaction of mixed phosphonium–iodonium ylide withp-methoxyphenylacetylene

Abstract: CIDNP in 31P NMR spectra of major products in the course of the reaction between phosphonium–iodonium ylide and p-methoxyphenylacetylene reveals the mechanism of products formation via radical pair.

Cited by 4 publications

References 20 publications

Spin Hyperpolarization in Modern Magnetic Resonance

Spin Hyperpolarization in Modern Magnetic Resonance

Trikoordinált jódvegyületek előállításainak és alkalmazásainak fejlesztése

Radicals in Annulation of Mixed Benzoyl Phosphonium‐Iodonium Ylide and Acetylenes Explored by EPR‐ST Spectroscopy

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