Ein N-alkoxy-N-vinylamino-radikal ungewoehnlicher stabilitaet

Ahrens, Wilhelm; Wieser, Karlheinz; Berndt, A.

doi:10.1016/s0040-4039(00)79793-0

Cited by 17 publications

(5 citation statements)

References 13 publications

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“…This last observation has been confirmed by others for quite a variety of alkoxyarylamino radicals,11-14 and an exceptionally persistent A-alkoxy-A-vinylamino radical has also been reported. 15 A-Alkoxyamino radicals have not been detected previously.…”

mentioning

confidence: 83%

Kinetic applications of electron paramagnetic resonance spectroscopy. 28. N-Alkoxy-N-alkylamino, N-alkoxyamino, and N-alkoxyanilino radicals

Kaba¹,

Ingold²

1976

J. Am. Chem. Soc.

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confidence: 83%

Kinetic applications of electron paramagnetic resonance spectroscopy. 28. N-Alkoxy-N-alkylamino, N-alkoxyamino, and N-alkoxyanilino radicals

Kaba¹,

Ingold²

1976

J. Am. Chem. Soc.

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“…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.…”

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confidence: 99%

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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“…Although a variety of N-alkoxyalkylaminyl (R ṄOR), [1][2][3] Nalkoxyvinylaminy 4 and N-alkoxyarylaminyl radicals (Ar ṄOR) 1,2,5-10 have been investigated for a long period and persistent N-alkoxyaminyls have been found, there are no reports of isolation of N-alkoxyaminyls. This is in contrast to the chemistry of thioaminyl radicals (R ṄSR).…”

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confidence: 99%

First isolation of N-alkoxyaminyl radicals

Miura

Tomimura

2001

Chem. Commun.

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Ein N-alkoxy-N-vinylamino-radikal ungewoehnlicher stabilitaet

Cited by 17 publications

References 13 publications

Kinetic applications of electron paramagnetic resonance spectroscopy. 28. N-Alkoxy-N-alkylamino, N-alkoxyamino, and N-alkoxyanilino radicals

Kinetic applications of electron paramagnetic resonance spectroscopy. 28. N-Alkoxy-N-alkylamino, N-alkoxyamino, and N-alkoxyanilino radicals

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

First isolation of N-alkoxyaminyl radicals

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Ein N-alkoxy-N-vinylamino-radikal ungewoehnlicher stabilitaet

Cited by 17 publications

References 13 publications

Kinetic applications of electron paramagnetic resonance spectroscopy. 28. N-Alkoxy-N-alkylamino, N-alkoxyamino, and N-alkoxyanilino radicals

Kinetic applications of electron paramagnetic resonance spectroscopy. 28. N-Alkoxy-N-alkylamino, N-alkoxyamino, and N-alkoxyanilino radicals

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

First isolation of N-alkoxyaminyl radicals

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