The cyano group as a facilitator of electron-transfer chain substitution processes

Kornblum, Nathan; Fifolt, Michael J.

doi:10.1021/jo01290a036

Cited by 21 publications

(10 citation statements)

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“…Moreover, recent investigations reveal the general phenomenon that certain substitution reactions occur as the chain anion-radical processes of the SrnI type. [99][100][101][102][103][104][105][106][107][108][109][110][111] In any case, the SET mechanism is often postulat-ed112-118 on the basis of the structure of the reaction products, but special studies are necessary to distinguish this mechanistic pathway. For example, a clue to the mechanism may be provided by the use of isotopically labeled compounds, as shown in eq 26.30…”

Section: Nucleophilesmentioning

confidence: 99%

X-philic reactions

Зефиров¹,

Makhon'kov²

1982

Chem. Rev.

201

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Section: Nucleophilesmentioning

confidence: 99%

X-philic reactions

Зефиров¹,

Makhon'kov²

1982

Chem. Rev.

201

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“…Three nitrogens from ligand 4d and aziridine 1b and one oxygen from 1b coordinate to nickel(II) in a distorted square planar manner, and activated α-nitromalonate 2b attacks aziridine. In general, the α-nitroester generally acts as a C-nucleophile; however, in this reaction, the α-nitroester reacted with aziridine by including oxygen in the nitro group . This result supports the assumption that the reaction proceeds in the coordination sphere of nickel(II).…”

mentioning

confidence: 99%

Enantioselective Oxidative Ring-Opening Reaction of Aziridines with α-Nitroesters Using Cinchona Alkaloid Amide/Nickel(II) Catalysts

et al. 2016

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The enantioselective oxidative ring-opening reaction of aziridines with α-nitroacetates has been developed. Good yields and enantioselectivity were observed for the reaction of various aziridines using a novel cinchona alkaloid amide/NiBr catalyst. Both enantiomers of products could be obtained by using pseudoenantiomeric chiral catalysts. This process offers an efficient route for the synthesis of α-aminoketones.

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“…On the basis of the available evidence, it appears that a nitro group is gen erally necessary for the Sg^^^l process at a saturated carbon. Although, a few examples are known where neither RX~ or RA" possess a nitro substituent [23]. accomplished under a variety of conditions [24] usually involving a positively polarized chlorine.…”

Section: Methodsmentioning

confidence: 99%

Free-radical clocks in the aliphatic S[subscript RN]1 process and reactions of nucleophiles with 1,1-dinitro-2,2-diphenylethylene

Dedolph

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The cyano group as a facilitator of electron-transfer chain substitution processes

Cited by 21 publications

References 0 publications

X-philic reactions

X-philic reactions

Enantioselective Oxidative Ring-Opening Reaction of Aziridines with α-Nitroesters Using Cinchona Alkaloid Amide/Nickel(II) Catalysts

Free-radical clocks in the aliphatic S[subscript RN]1 process and reactions of nucleophiles with 1,1-dinitro-2,2-diphenylethylene

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