Ketene. Part 23. Conformational control of the addition reactions of ketenes with N-phenylnitrones

Falshaw, C. P.; HASHI, N. A.; Taylor, Giles A.

doi:10.1039/p19850001837

Cited by 26 publications

(11 citation statements)

References 3 publications

(4 reference statements)

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“…In both cases the relatively short C=N and the long N-0 bond distances indicate an increased iminium salt character of the nitrone moiety within a B ,N-betaine complex. The C=N bond lengths in free (uncomplexed) nitrones are somewhat longer in most cases while the N-0 bonds are generally shorter (17)(18)(19)(20)(21)(22).…”

Section: Resultsmentioning

confidence: 99%

Structural studies of organoboron compounds. XXVI. 8-Methyl-6,6-diphenyl-5,7-dioxa-8-azonia-6-borata-6,7-dihydro-5H-benzocycloheptene

Kliegel¹,

Rettig²,

Trotter³

1987

Can. J. Chem.

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. Can. J. Chem. 65, 1457Chem. 65, (1987. Crystals of 8-methyl-6,6-diphe~yl-5,7-dioxa-8-azonia-6-borata-6,7-dihydro-5H-be11~0~ycloheptene are triclijc, a = 12.917(1), b = 13.285(1), c = 10.567(1) A, a = 94.183(8), P = 90.094(5), y = 72.176(6)", Z = 4, space group P 1. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.045 and R,,, = 0.042 for 2914 reflections with I 2 2u(I). The envelope-like conformation adopted by the seven-membered chelate ring places one B-phenyl group above the plane of the fused-ring system facilitating a thermally-induced 1,4-migration of a B-phenyl group to the nitrone carbon atom. Mean bond lengths (corrected for libration) are (N)O-B = 1.559 (6)

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Section: Resultsmentioning

confidence: 99%

Structural studies of organoboron compounds. XXVI. 8-Methyl-6,6-diphenyl-5,7-dioxa-8-azonia-6-borata-6,7-dihydro-5H-benzocycloheptene

Kliegel¹,

Rettig²,

Trotter³

1987

Can. J. Chem.

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“…Interestingly, (I) is found to be isomorphic with ,-Ntriphenylnitrone, a structural isomer of (I), reported by Brown & Trefonas (1973) (s.u. values = 0.005 Å on distances and 0.03 on angles) and Falshaw et al (1985). However, the two compounds are chemically significantly different.…”

Section: Commentmentioning

confidence: 95%

N,N-Diphenylbenzamide

2010

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In the title compound, C(19)H(15)NO, the neutral molecules are held together in the crystal structure by very weak C-H...O interactions, giving rise to a linear chain-like structure. The structure of the molecule has been optimized using density functional theory at the B3LYP/6-31G(d) level and this is compared with the molecular structure in the solid state. The two structures show significant differences in the relative orientations of the aromatic rings, which is interesting for further supramolecular study. Apart from the crystal structure analysis, powder X-ray diffraction, UV-visible and thermogravimetric analyses of the compound have been carried out.

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“…Indeed, X-ray crystal structures of sterically hindered C-arylsubstituted nitrones show that the aryl groups are twisted out of the plane of the C¼ ¼NO p system. [194][195][196][197][198][199][200][201][202][203][204] To probe the conformations, degrees of conjugation, and thermal stabilities of sterically hindered aryl nitrones, a series of substituted nitrones was prepared. BPN was prepared by the simple condensation of t-butyl hydroxylamine (generated in situ by zinc metal reduction of 2-methyl-2-nitropropane) and benzaldehyde in a 42% yield after flash chromatography.…”

Section: Scheme 18mentioning

confidence: 99%

Nitroxide decomposition: Implications toward nitroxide design for applications in living free‐radical polymerization

Nilsen

Braslau

2005

J. Polym. Sci. A Polym. Chem.

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ABSTRACT:Nitroxides bearing an a-hydrogen decompose upon heating in a bimolecular reaction. A new mechanism is proposed for the decomposition of t-butylisopropylphenyl nitroxide (TIPNO) involving the formation of a head-to-tail dimer, single electron transfer to form an oxammonium salt, epimerization to the corresponding nitrone, and elimination to form a conjugated oxime. This mechanism may provide insights into designing new nitroxides for use in controlled polymerization.

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Ketene. Part 23. Conformational control of the addition reactions of ketenes with N-phenylnitrones

Cited by 26 publications

References 3 publications

Structural studies of organoboron compounds. XXVI. 8-Methyl-6,6-diphenyl-5,7-dioxa-8-azonia-6-borata-6,7-dihydro-5H-benzocycloheptene

Structural studies of organoboron compounds. XXVI. 8-Methyl-6,6-diphenyl-5,7-dioxa-8-azonia-6-borata-6,7-dihydro-5H-benzocycloheptene

N,N-Diphenylbenzamide

Nitroxide decomposition: Implications toward nitroxide design for applications in living free‐radical polymerization

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