Ueber die Condensation von Mandelsäure mit Phenolen

Bistrzycki, A.; Flatau, J.

doi:10.1002/cber.189502801217

Cited by 35 publications

(7 citation statements)

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“…From these experiments, we also conclude that it is the lowlying singlet state of 14 which is trapped by oxygen and which undergoes exchange with the protic solvent. As was pointed out earlier, a significant concentration (ca.…”

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confidence: 70%

“…Support for this supposition is provided by the observation that, in contrast to the direct irradiation oxygenations, lactone 1 is inert to photosensitized oxygenations (Rose Bengal) when the solvent used is acetonitrile, cyclohexane, or benzene. This observation would tend to support a scheme which involves reaction of the excited enolate anion (14) with ground-state oxygen (see Scheme I) in these solvent systems. Only in methanol does 1 exist to any appreciable extent as the enolate tautomer (ca.…”

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confidence: 74%

“…30%. This would imply that the equilibrium between the keto and enolate tautomer (14) was shifted more toward the keto form in the deuterated system. Consequently, the quantum yield for the photooxygenation of 1 would be expected to diminish on deuterium exchange.…”

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confidence: 99%

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Photochemical transformations of small ring heterocyclic compounds. LXII. Competitive keto-enolate photochemistry in the 3-phenylcoumaran-2-one system

Padwa¹,

Dehm²,

Oine³

et al. 1975

J. Am. Chem. Soc.

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confidence: 70%

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confidence: 74%

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Photochemical transformations of small ring heterocyclic compounds. LXII. Competitive keto-enolate photochemistry in the 3-phenylcoumaran-2-one system

Padwa¹,

Dehm²,

Oine³

et al. 1975

J. Am. Chem. Soc.

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“…The first and simplest congener of this class, the 3phenylben zofuran2on 10 (Scheme 4), was prepared in 1896 by the founder [28] of the chemistry department of the University of Fribourg in Switzerland, Augustin Bistrzycki. His synthesis [29] consisted of the condensa tion of phenol with mandelic acid in 73% H 2 SO 4 and afforded 10 in a modest 22% yield. In 1977 Karafiloglou et al [30] re ported the electron spin resonance (ESR) study of the blue persistent benzofuranyl radical 11, which is in thermal equilibrium with its dimer 12.…”

Section: Stabilization Of Polymers During Processingmentioning

confidence: 99%

Radicals and Polymers

Nesvadba¹

2018

Chimia

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This article describes some selected results of my 30 years as an industrial researcher. During this time, I had the chance to work on many very different projects. About two thirds of them were dealing with the fascinating interaction of radicals and polymers. Of the more than 350 million tons of industrial polymers produced worldwide every year, about 50% are made by the radical polymerization of monomers that are often stabilized against undesired premature polymerization by addition of polymerization inhibitors. Stabilizers are necessary to protect the majority of polymeric materials during their service life from radical degradation processes triggered by oxygen, heat or light. Modification of the polymeric architecture can be easily achieved via radical polymer analogous reactions. One of the most important developments in polymer science in the last 25 years is controlled radical polymerization. Recently, radical bearing redox-active polymers emerged as promising in energy storage applications, for example, in organic radical batteries. Our contributions to the fields mentioned above are described with examples of: a) novel benzofuranone stabilizers for polymers; b) the serendipidous discovery of novel dyestuffs; c) eco-friendly polymerization inhibitors; d) novel nitroxides and alkoxyamines for the first industrial realization of controlled radical polymerization; e) novel and safe radical initiators; f) nitroxide radicals bearing polymers for electrochemical applications.

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“…The foregoing experiment was carried out without rigid exclusion of oxygen, and 3 The melting point reported by these authors was 70°. 4 The 2,4,6-triisopropylbenzene used was Alkazene-13 obtained from the Dow Chemical Company. through the ether solution of the product (enol) a stream of air was passed for one hour.…”

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confidence: 99%