A convenient nitroxide radical synthesis

Motherwell, W. B.; Roberts, J. S.

doi:10.1039/c39720000328

Cited by 19 publications

(2 citation statements)

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“…The nature of the products depends on the method used and on the ability of the solvent to act as an H* donor. It has also been suggested (295,296) that hydroxyaminyl radicals, e.g., 121 (296), cyclize directly. It has also been suggested (295,296) that hydroxyaminyl radicals, e.g., 121 (296), cyclize directly.…”

Section: E Alkenoxy Alken Aminyi and Other Heteroatom-centered Radimentioning

confidence: 99%

Free-Radical Rearrangements

Beckwith¹,

Ingold²

1980

Organic Chemistry: A Series of Monographs

114

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Section: E Alkenoxy Alken Aminyi and Other Heteroatom-centered Radimentioning

confidence: 99%

Free-Radical Rearrangements

Beckwith¹,

Ingold²

1980

Organic Chemistry: A Series of Monographs

114

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“…Reduction of the nitrocompound by Zn/NH 4 Cl and subsequent oxidation of enehydroxylamine 186 by Ag 2 CO 3 /celite or Ag 2 O allows us to obtain the target nitroxide 183 in a 30% yield. The authors suggested that the precursor of SNR 183 is open-chain monoalkyl nitroxide 187 , which can undergo cyclization similarly to a certain olefinic aminium radical cation ( Scheme 33 ) [ 143 ].…”

Section: 25-dihydropyrrole (3-pyrroline)- and Pyrrolidine (Proxylmentioning

confidence: 99%

Spirocyclic Nitroxides as Versatile Tools in Modern Natural Sciences: From Synthesis to Applications. Part I. Old and New Synthetic Approaches to Spirocyclic Nitroxyl Radicals

Zaytseva

Mazhukin

2021

Molecules

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Spirocyclic nitroxyl radicals (SNRs) are stable paramagnetics bearing spiro-junction at α-, β-, or γ-carbon atom of the nitroxide fragment, which is part of the heterocyclic system. Despite the fact that the first representatives of SNRs were obtained about 50 years ago, the methodology of their synthesis and their usage in chemistry and biochemical applications have begun to develop rapidly only in the last two decades. Due to the presence of spiro-function in the SNRs molecules, the latter have increased stability to various reducing agents (including biogenic ones), while the structures of the biradicals (SNBRs) comprises a rigid spiro-fused core that fixes mutual position and orientation of nitroxide moieties that favors their use in dynamic nuclear polarization (DNP) experiments. This first review on SNRs will give a glance at various strategies for the synthesis of spiro-substituted, mono-, and bis-nitroxides on the base of six-membered (piperidine, 1,2,3,4-tetrahydroquinoline, 9,9′(10H,10H′)-spirobiacridine, piperazine, and morpholine) or five-membered (2,5-dihydro-1H-pyrrole, pyrrolidine, 2,5-dihydro-1H-imidazole, 4,5-dihydro-1H-imidazole, imidazolidine, and oxazolidine) heterocyclic cores.

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Silver(I) Carbonate on Celite

Fétizon

2001

Encyclopedia of Reagents for Organic Synthesis

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A convenient nitroxide radical synthesis

Cited by 19 publications

References 0 publications

Free-Radical Rearrangements

Free-Radical Rearrangements

Spirocyclic Nitroxides as Versatile Tools in Modern Natural Sciences: From Synthesis to Applications. Part I. Old and New Synthetic Approaches to Spirocyclic Nitroxyl Radicals

Silver(I) Carbonate on Celite

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