C-nitroso compounds—II

Wajer, Th. A. J. W.; Mackor, A.; Boer, Th. J. de; Voorst, J.D.W. van

doi:10.1016/s0040-4020(01)97911-6

Cited by 65 publications

(10 citation statements)

References 12 publications

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“…exhibit this restricted rotation (27,28) which holds the -NO group and the benzene ring coplanar for a time longer than ca. lop6 s for the former, or for a time comparable to lop6 s for the latter.…”

Section: Radicals Fornzulated As R-ii-0-r'mentioning

confidence: 99%

Electron paramagnetic resonance spectroscopic study of nitroxide radicals formed from oximes

Smith¹,

Fox²

1969

Can. J. Chem.

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The addition of hydroxyl radicals to each of the oximes, acetaldoxime, acetoxime, and 2,3-butanedione monoxime, has been studied by mixing titanous chloride, hydrogen peroxide, and the oxime in a n aqueous continuous-flow system. I n each case a p-hydroxy nitroxide (functional structure )c(oH)-NH-0.) is formed. I n confirmation of these results, amino and hydroxymethyl radicals we; e added to the oximes using similar procedures to give in each case the radicals of functional structure >c(NH,)-NH-0. and )C(CH~OH)-NH-o., respectively. Attempts to add methyl radicals, prepared by the reaction betwGen titanous chloride and t-butyl hydroperoxide, to these oximes gave no observable products save the methyl radicals. However, use of titanous chloride and peracetic acid gave results consistent with the addition of hydroxyl radicals. The addition of hydroxyl radicals to the oxime-0-methyl ethers of acetaldehyde and acetone gave radicals of functional structure 'c(oH)-N-0-CH, / (JaNl, ca. 14 G ; a,,0CH3~, ca. 3 G ) which have not previously been identified unambiguously. On the assumption that JQNl = lQHNH = 23 G in all these radicals, pNn has been calculated and used to obtain a value for lQHO H~I of ca. 11 G whlch is within the range of other estimates in the literature.

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Section: Radicals Fornzulated As R-ii-0-r'mentioning

confidence: 99%

Electron paramagnetic resonance spectroscopic study of nitroxide radicals formed from oximes

Smith¹,

Fox²

1969

Can. J. Chem.

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“…In all cases, when the reactants were mixed, the ESR spectrum showed a triplet signal of di tert butylnitroxyl radical [6] with parameters a N = 15.1 Oe and g = 2.0060, which is generated in the course of the photolytic transformation of MNP.…”

Section: Resultsmentioning

confidence: 94%

Azobis(isobutyronitrile)–Tri-n-butylborane radical-producing system in methyl methacrylate Polymerization

et al. 2015

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“…When the temperature is further increased to 70 °C, the M n greatly decreased. The main reason is that MNP is volatile and easy to photodecompose to tert ‐butyl radical and nitric oxide …”

Section: Resultsmentioning

confidence: 99%

Radical addition-coupling polymerization with various nitroso compounds

Wang

2013

J. Polym. Sci. Part A: Polym. Chem.

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Four nitroso esters were prepared by oxidation of 4,4-dimethyl dihydro-1,3-oxazine or 4,4-dimethyl-2-oxazoline with two equiv of m-chloroperoxybenzoic acid. All of them can be applied in radical addition-coupling polymerization to produce periodic polymer together with introduction of ester group at side chain. Compared with 2-methyl-2-nitrosopropane, 2-nitroso-2-methyl-4-acetoxypentane and 2-methyl-2-nitrosopropyl hexanoate present good stability at high temperature up to 70 C and can result polymer with high molecular weight. KEYWORDS: atom transfer radical polymerization; functionalization of polymers; nitroso ester; radical addition-coupling polymerization; step-growth polymerization INTRODUCTION Radical addition-coupling polymerization (RACP) has been proposed for synthesis of periodic polymer with regular monomer sequence. [1][2][3] As shown in Scheme 1, the polymerization involves consecutive addition of carboncentered radical to N@O of C-nitroso compound followed by cross-coupling of carbon-centered radical and in situ formed nitroxyl radical, which produces copolymers with high molecular weight and unimodal molecular weight distribution from saturated and unsaturated monomers. The key step of RACP is the formation of intermediate nitroxyl radical, which is stable enough to take cross-coupling reaction with relatively active carbon-centered radical based on persistent radical effect. 4 The N@O double bond plays an essen-

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C-nitroso compounds—II

Cited by 65 publications

References 12 publications

Electron paramagnetic resonance spectroscopic study of nitroxide radicals formed from oximes

Electron paramagnetic resonance spectroscopic study of nitroxide radicals formed from oximes

Azobis(isobutyronitrile)–Tri-n-butylborane radical-producing system in methyl methacrylate Polymerization

Radical addition-coupling polymerization with various nitroso compounds

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