Ein einfacher weg zu spinaddukten aus nitrosoverbindungen und t-butyl-radikalen; ungewoehnlich stabile n-alkoxy-anilino-radikale

Ahrens, Wilhelm; Berndt, A.

doi:10.1016/s0040-4039(01)87171-9

Cited by 23 publications

(5 citation statements)

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“…On the basis of the above results, we conclude that the present N -alkoxyarylaminyls are thermally very stable. Previously, it was reported that N - tert -butoxy-2,6-diphenyl-4- tert -butylphenylaminyl ( 18 ) rearranged to the corresponding aminoxyls at room temperature . Since 18 is structurally very similar to 2 , we are interested in this difference.…”

Section: Resultsmentioning

confidence: 99%

“…Although a variety of N -alkoxyalkylaminyls (RṄOR), − N -alkoxyvinylaminyls, and N -alkoxyarylaminyls (ArṄOR) 2-4,6-10 have widely been investigated by ESR spectroscopy over a long period and some persistent N -alkoxyaminyls have been found, there have been no reports of isolation of N -alkoxyaminyls. This is in contrast to the chemistry of isoelectronic thioaminyl radicals (RṄSR). , Since the first ESR studies on N -(phenylthio)phenylaminyl (PhṄSPh) were independently reported by two groups, a number of studies on thioaminyls have been carried out and their electronic structures, stabilities (lifetimes), and decomposition mechanism have widely been elucidated.…”

Section: Introductionmentioning

confidence: 99%

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First Isolation of Monomeric N-Alkoxyarylaminyl Radicals and Their Chemical and Magnetic Properties¹

et al. 2001

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The present report describes the first isolation of monomeric N-alkoxyarylaminyls and their chemical and magnetic properties. Reaction of the corresponding lithium amides of 2,4-diaryl-6-tert-butylanilines, 2,6-diaryl-4-tert-butylanilines, or 2,4,6-triarylanilines with tert-butyl peroxybenzoate in THF at -78 degrees C yielded quite persistent N-tert-butoxy-2,4-diaryl-6-tert-butylphenylaminyls (1), N-tert-butoxy-2,6-diaryl-4-tert-butylphenylaminyls (2), and N-tert-butoxy-2,4,6-triarylphenylaminyls (3), respectively, which were isolated in the monomeric form in 17-25% yields. All radicals prepared were oxygen insensitive and thermally very stable. X-ray crystallographic analyses were carried out for two radicals, and it was shown that the N and O atoms are coplanar with the anilino benzene ring. The ESR spectra of 1-3 gave a(N) = 0.984-1.05 and a(H) (anilino meta) = 0.158-0.170 mT (g = 2.0041-2.0043), indicating that the unpaired electron mainly resides on the nitrogen and anilino benzene ring. Magnetic susceptibility measurements for 1 and 3 showed that one radical revealed a weak ferromagnetic interaction and an analysis by the Curie-Weiss law gave 0.3 K as theta. The other radicals examined showed weak antiferromagnetic interactions and theta's were determined to be -0.3 to -1.5 K.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

First Isolation of Monomeric N-Alkoxyarylaminyl Radicals and Their Chemical and Magnetic Properties¹

et al. 2001

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“…N-Alkoxyarylaminyls 1 were stable in solution, even in the presence of atmospheric oxygen and, although 1a was heated at 80 °C in degassed benzene for 10 d, 80% of the radical survived and no rearrangement to the corresponding aminoxyl 2 was observed. 8,16 These observations indicate that 1 is an oxygen insensitive and thermally stable radical.…”

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confidence: 84%

First isolation of N-alkoxyaminyl radicals

Miura

Tomimura

2001

Chem. Commun.

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“…Such an eventuality was shown by EPR on an example of aromatic nitro compounds. 24 For PVP the process resulting in radicals 2 can be presented as follows (reaction ( 11)):…”

Section: Influence Of Spectral Composition Of Light On Kinetics and M...mentioning

confidence: 99%

Aminoxyl radicals as crosslinks for macromolecules of polyvinylpyrrolidone

et al. 2004

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Using polyvinylpyrrolidone as an example, it has been shown that photolysis of ceric ammonium nitrate at room temperature can result in crosslinking of macromolecules. This process correlates with the formation of stable aminoxyl radicals, which are registered by EPR. The mechanism involves photodissociation of nitrate radicals produced in the primary reaction into nitric oxide or nitrogen dioxide depending on the wavelength of the light, and simultaneous formation of macroradicals. The accumulation of aminoxyl radicals occurs owing to the acceptance of macroradicals by nitroso or nitro groups according to which mechanism of the nitrate radical photodissociation prevails. Similar radical reactions are observed in N-methyl-2-pyrrolidone.

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Ein einfacher weg zu spinaddukten aus nitrosoverbindungen und t-butyl-radikalen; ungewoehnlich stabile n-alkoxy-anilino-radikale

Cited by 23 publications

References 9 publications

First Isolation of Monomeric N-Alkoxyarylaminyl Radicals and Their Chemical and Magnetic Properties¹

First Isolation of Monomeric N-Alkoxyarylaminyl Radicals and Their Chemical and Magnetic Properties¹

First isolation of N-alkoxyaminyl radicals

Aminoxyl radicals as crosslinks for macromolecules of polyvinylpyrrolidone

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Ein einfacher weg zu spinaddukten aus nitrosoverbindungen und t-butyl-radikalen; ungewoehnlich stabile n-alkoxy-anilino-radikale

Cited by 23 publications

References 9 publications

First Isolation of Monomeric N-Alkoxyarylaminyl Radicals and Their Chemical and Magnetic Properties1

First Isolation of Monomeric N-Alkoxyarylaminyl Radicals and Their Chemical and Magnetic Properties1

First isolation of N-alkoxyaminyl radicals

Aminoxyl radicals as crosslinks for macromolecules of polyvinylpyrrolidone

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First Isolation of Monomeric N-Alkoxyarylaminyl Radicals and Their Chemical and Magnetic Properties¹

First Isolation of Monomeric N-Alkoxyarylaminyl Radicals and Their Chemical and Magnetic Properties¹