Reaktionen freier radikale mit metallorganischen verbindungen, II Das radikalsystem 2.4.6-tri-tert.-butyl-phenoxyl/triphenylaluminium

Müller, Eugen; Ziemek, Peter; Rieker, Anton

doi:10.1016/0040-4039(64)80004-6

Cited by 11 publications

(3 citation statements)

References 1 publication

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“…An intermediate complex was postulated to explain the products. basis of ¿its esr spectrum, an aluminum radical was present and structure AL was suggested for it (241).…”

Section: Arormentioning

confidence: 99%

The Chemistry of Stable Phenoxy Radicals

Altwicker¹

1967

Chem. Rev.

265

189

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are closely related to phenoxy radicals but have a unique structural feature in that they are radical anions, will be mentioned only briefly. The chemistry of semiquinones has been the subject of an earlier review paper (202; for recent references cf. 58, 208, 313). Stable radicals based on polynuclear phenols (such as naphthols etc.) will be discussed.Electron spin resonance spectroscopy has contributed more than any other tool to the structural analysis of phenoxys and to the characterization of many new radicals. The results from esr work will be introduced where pertinent, but a detailed discussion of the many spectra that have been published is considered beyond the scope of this review. Excellent summaries of the esr method (232,325) and its application to phenoxy radicals have appeared (44,205).The literature has been reviewed through September 1966; a number of later references are included. III. Generation of Phenoxy RadicalsA.

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“…An intermediate complex was postulated to explain the products. basis of ¿its esr spectrum, an aluminum radical was present and structure AL was suggested for it (241).…”

Section: Arormentioning

confidence: 99%

The Chemistry of Stable Phenoxy Radicals

Altwicker¹

1967

Chem. Rev.

265

189

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“…It remains unclear what compounds are formed in the reactions of 2,6 Bu t 2 C 6 H 3 OH with alkali alkoxides or hydroxides, and no data on the structure, properties, and reactivity of individual alkali 2,6 di tert butylphen oxides are available. In the patent 5 2,6 di tert butyl phenoxides are described as monomers, whereas other literature sources 14,15 show that some derivatives of 2,6 di tert butylphenoxides exist as dimers. Therefore, it seems of interest to reveal the true structure of 2,6 Bu t 2 C 6 H 3 OK and 2,6 Bu t 2 C 6 H 3 ONa and optimize the method of their synthesis.…”

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confidence: 98%

Potassium and sodium 2,6-di-tert-butylphenoxides and their properties

Володькин

Заиков

2006

Russ Chem Bull

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The crucial factor of the reaction of 2,6 di tert butylphenol with alkali hydroxides is temperature, depending on which two types of potassium or sodium 2,6 di tert butylphenoxides are formed. These types exhibit different catalytic activity in the alkylation of 2,6 di tert butylphenol with methyl acrylate. More active forms of 2,6 Bu t 2 C 6 H 3 OK or 2,6 Bu t 2 C 6 H 3 ONa are synthesized at temperatures higher than 160 °C and are predominantly the monomers, which dimerize on cooling. The data of 1 H NMR, electronic, and IR spectra for the corre sponding forms of 2,6 Bu t 2 C 6 H 3 OK and 2,6 Bu t 2 C 6 H 3 ONa isolated in the individual state are in agreement with cyclohexadienone structure. In DMSO or DMF, the dimeric forms of 2,6 di tert butylphenoxides react with methyl acrylate to form methyl 3 (4 hydroxy 3,5 di tert butylphenyl)propionate in 64-92% yield.

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“…It remains unclear what compounds are formed in the reactions of 2,6-Bu t 2 C 6 H 3 OH with alkaline metal alkoxides or hydroxides, and no data on the structure, properties, and reactivity of individual alkaline metal 2,6di-tert-butylphenoxides are available. In the patent [5] 2,6di-tert-butylphenoxides are described as monomers, whereas other literature sources [14,15] show that some derivatives of 2,6-di-tert-butylphenoxides exist as dimers. Therefore, it seems of interest to reveal the true structure of 2,6-Bu t 2 C 6 H 3 OK and 2,6-Bu t 2 C 6 H 3 ONa and optimize the method of their synthesis.…”

Section: Introductionmentioning

confidence: 99%

Potassium and Sodium 2,6-Di-tert-Butyl Phenoxides and their Properties

́kin¹,

Заиков²

2010

ChChT

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The determining factor of the reaction of 2,6-di-tert-butylphenol with alkaline metal hydroxides is temperature, depending on which two types of potassium or sodium 2,6-di-tert-butyl phenoxides are formed with different catalytic activity in alkylation of 2,6-di-tert-butylphenol with methyl acrylate. More active forms of 2,6-But2C6H3OK or 2,6-But2C6H3ONa are synthesized at temperatures higher than 433 K representing predominantly monomers of 2,6-di-tert-butylphenoxides which produce dimers when cooling. The data of NMR 1Н, electronic, and IR spectra for the corresponding forms of 2,6-But2C6H3OK and 2,6-But2C6H3ONa isolated in the individual state showed a cyclohexadienone structure. In DMSO or DMF media the dimeric forms of 2,6-di-tert-butylphenoxides react with methyl acrylate to form methyl 3-(4-hydroxy-3,5-di-tert-butylphenyl) propionate with 64–92 % yield.

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Reaktionen freier radikale mit metallorganischen verbindungen, II Das radikalsystem 2.4.6-tri-tert.-butyl-phenoxyl/triphenylaluminium

Cited by 11 publications

References 1 publication

The Chemistry of Stable Phenoxy Radicals

The Chemistry of Stable Phenoxy Radicals

Potassium and sodium 2,6-di-tert-butylphenoxides and their properties

Potassium and Sodium 2,6-Di-tert-Butyl Phenoxides and their Properties

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