Fragmentation of oxyalkyl radicals: A new general route to nitrogen radicals

Forrester, A. R.; Gill, Melvin; Johansson, Eva; Meyer, Catherine; Thomson, R. H.

doi:10.1016/s0040-4039(01)83304-9

Cited by 6 publications

(4 citation statements)

References 7 publications

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“…color. The same intermediate was proposed for the Nef reaction whereby nitroalkanes have been hydrolyzed by acids into carbonyl compounds.60® Nitrosonium430,431 and nitronium431 salts converted oximes into corresponding aldehydes and ketones with comparable efficiencies (53% to 84% yields) (eq 424,425). Product forma-…”

Section: Iminylsmentioning

confidence: 85%

“…Oxidation of oxime methyl ethers (R2C=NOCH3) with diferf-butyl peroxide did not produce oxaziridines: the only product reported was an iminoxylakyl radical (R2C=NOCH2*) 424 On the other hand, oxidation of cyclic imidates 521 and 522 gave thermally unstable bicyclic oxaziridines 523 and 524 (eq 419). Each decomposed violently on concentration.423 3.…”

Section: Keteniminesmentioning

confidence: 99%

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Increasing the index of covalent oxygen bonding at nitrogen attached to carbon

Boyer¹

1980

Chem. Rev.

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Section: Iminylsmentioning

confidence: 85%

Section: Keteniminesmentioning

confidence: 99%

Increasing the index of covalent oxygen bonding at nitrogen attached to carbon

Boyer¹

1980

Chem. Rev.

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“…The usual route to ketiminyls, which involves hydrogen abstraction from ketimines (12), was inapplicable since cyclopentylketimine appears to be unknown. Other routes to ketiminyl radicals are known (13,14) but none of those we investigated proved suitable.…”

Section: Introductionmentioning

confidence: 99%

Cyclization of the 4-cyanobutyl radical

Griller¹,

Schmid²,

Ingold³

1979

Can. J. Chem.

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. INGOLD. Can. J. Chem. 57,831 (1979). The rate constant for the irreversible cyclization of the 4-cyanobutyl radical to the cyclopentiminyl radical, kcCzN, has been measured from -52 to 12°C by kinetic epr spectroscopy. The temperature dependence of this rate constant can be represented by, log (k,C'N/s-') = (9.9 2 1.0) -(8.6 t l.0)/8 where 8 = 2.3RT kcal/mol. This rearrangement is somewhat slower than the analogous cyclizations of the 5-hexenyl and 5-hexynyl radicals.DAVID GRILLER, PETER SCHMID et KEITH U. INGOLD. Can. J. Chem. 57,831 (1979). On a mesurk les constantes de vitesse de la cyclisation irrtversible du radical cyano-4 butyle en radical cyclopentiminyle, kcCEN, a des tempkratures allant de -52 a 12°C en faisant appel a la spectroscopie rpe. On peut reprtsenter la relation entre la constante de vitesse et la temptrature grlce a l'tquation oh 0 = 2.3RT kcal/mol. Cette transposition est un peu plus lente que les cyclisations analogues des radicaux hexenyle-5 et hexynyle-5.[Traduit par le journal]

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“…Examples include silyl (90, 90a, 101, 362), e.g., PhCH 2 CH 2 CH 2 SiMe 2 , alkoxy (363,364), carboxylate (93,365,366), acyl (356), iminyl, e.g., 167 -* 168 (367), amidyl (334,(368)(369)(370), aminium (371, 371a), and thiyl (372) radicals. Examples include silyl (90, 90a, 101, 362), e.g., PhCH 2 CH 2 CH 2 SiMe 2 , alkoxy (363,364), carboxylate (93,365,366), acyl (356), iminyl, e.g., 167 -* 168 (367), amidyl (334,(368)(369)(370), aminium (371, 371a), and thiyl (372) radicals.…”

mentioning

confidence: 99%