Über den peroxydischen Abbau von substitutierten aromatischen Aldehyden und Ketonen zu den entsprechenden Phenolen

Wacek, A.; Eppinger, Hans

doi:10.1002/cber.19400730613

Cited by 13 publications

(11 citation statements)

References 33 publications

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“…A methoxyl group in the meta position does not lead to phenol formation when benzaldehydes are ozonized (68).…”

Section: A Ozonementioning

confidence: 95%

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Cleavages and Rearrangements Involving Oxygen Radicals and Cations.

Leffler¹

1949

Chem. Rev.

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“…A methoxyl group in the meta position does not lead to phenol formation when benzaldehydes are ozonized (68).…”

Section: A Ozonementioning

confidence: 95%

“…and Eppinger(68) proposed a similar mechanism for the Dakin reaction (alkaline hydrogen peroxide): supported by the fact that phenol is oxidized by hydrogen peroxide to hydroquinone and catechol.…”

mentioning

confidence: 90%

Cleavages and Rearrangements Involving Oxygen Radicals and Cations.

Leffler¹

1949

Chem. Rev.

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“…Migratory aptitudes of alkoxylated aryl groups are great and rearrangement (CLXVI) should occur readily to give CLXV, which should decompose to CLXIV. The aldehydes (CLXII) obtained as "normal" ozonolysis products also react with ozone to give phenols (525,559). This was shown not to be the principal source of the phenols, however, by the fact that in most cases the yield of a given phenol was less by ozonation of the corresponding aldehyde than by ozonolysis of the cinnamate (525,559).…”

Section: CLIIImentioning

confidence: 99%

“…The aldehydes (CLXII) obtained as "normal" ozonolysis products also react with ozone to give phenols (525,559). This was shown not to be the principal source of the phenols, however, by the fact that in most cases the yield of a given phenol was less by ozonation of the corresponding aldehyde than by ozonolysis of the cinnamate (525,559). Compound CLXIV, for example, was obtained in 48 per cent yield from CLVIII and in 4 per cent yield from CLXII.…”

Section: CLIIImentioning

confidence: 99%

The Reactions Of Ozone With Organic Compounds

Bailey¹

1958

Chem. Rev.

586

236

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“…In the case of p-hyclroxybenzaldehyde, osidation with an allialine solution of hydrogen peroxide produced a nearly quantitative yield of hydroquinone, together with formic acid from the alcleh~dic group. Waceli and his collaborators (30,31) discussed the probable mechanism of such oxidations, and isolated the monoformy1 ester of hydroquinoile as a n internlecliate when the osiclation was carried out wit11 pcracetic acid in acetic anhydride. The same type of osidation could be effected by a fe\v other peroxides (2), and also by ozonicles decomposing in alkali (30) b u t not by the other common oxidants tried.…”

mentioning

confidence: 99%

Studies in the Polyoxyphenol Series: Viii. The Oxidation of Substances Related to Vanillin With Sodium Chlorite and Chlorine Dioxide

Logan¹,

Husband²,

Purves³

1955

Can. J. Chem.

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The research confirmed the fact that chlorine dioxide and sodiu~n chlorite were not equivalent i11 their oxidizing properties. At 22' C. or less, the oxidation of pyrogallol by aqueous s o c l i~~~n chlorite a t pH 6 was very slow, but became very rapid on the acid side of pH 3.5. The amorphous, colored products probably did not include purpurogallin. Under similar circumsta~lces p-h~~drosybenzaldehyde was unaffected a t pH 6 ; 22% was oxidized t o p-benzoquino~le (Dalcin's reaction) a t pH 5, and this amount increased to 39y0 a t pH 1. The yield of benzoquinone was about 24% regardless of pH within the above range when aqueous chlorine dioxide was the oxidant. Sodiunl chlorite a t pH 0.9 produced a 91% yield of rnethoxy-p-quinone from 1nethoxy-p-hydroq~1i11011e; a t pH 4 this product was nixed with 56% of 4,4'-dirnethoxydiq~~inone, but near pH 6 a slower oxidation did not proceed beyo~ld 4,4'-dimethoxyquinhpdrone. Aqueous chlorine dioxide yielded a t least 02y0 of monomeric methoxyquinone a t all pH values between 1 and 6, probably in accord with the equation, 3 hydroquinonef3 C102+ 3 quinonef2 HCIfHCIO3 ( f 3 O f 3 H).The simultaneous formation of hydrogen peroxide mas suspected, but not proved.In sharp distinction to the behavior of free phenols, veratraldehyde was not oxidized by aqueous chlorine dioxide between pH 6 and pH 3, but a t pH 1 a slov reaction yielded up to 15% of veratric acid. Sodium chlorite produced about 02% of the same acid a t pH 1 and pH 4, but its action was negligible a t pH 5.Since by-product chlorine dioxide was ineffective a t pH 4, it was possible t o confirm the validity of the Jcanes-Isbell equation for the reduction of chlorous acid: CGH~(OCH~)UCI-IOfS HCIO2-> C~I-la(OCH~)~COOH+2 ClO~+HCI+H?O. The oxidation of acetyl;~ted vanillin was complicated by the occurrence of deacetylation. Red, chlorinated oils with quinoidal properties were also formed in most of the above oxiclatio~ls.Although aqueous solutions of sodium chlorite and of chlorine dioxide have often been coilsidered to be equivalent in their bleaching action, a recent research (11) sho.vvecl that they oxidized vanillin in somewhat different ways. Oxidations with chlorine dioxide a t 20' C. seemed to be independent oi the hydrogen ion concentration between pI-I 1 and pH G and did not alter the aldehyde group in vanillin. Sodium chloi-ite, however, had no effect a t pI-I 6 , produced about 18y0 of 5-chlorovanillin a t pH 5 , appeared to duplicate the behavior of chlorine dioxide a t pH 4, and produced derivatives of vanillic acid a t pI-I 3 or less. In order to determine the characteristics ot the two oxidants more fully, their action on several other phenolic substances has now been studied. Schmidt, and Sperliil (27) observed that an excess of chlorine clioxide in presence of a vanadium chloride catalyst produced about yields of 1

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Über den peroxydischen Abbau von substitutierten aromatischen Aldehyden und Ketonen zu den entsprechenden Phenolen

Cited by 13 publications

References 33 publications

Cleavages and Rearrangements Involving Oxygen Radicals and Cations.

Cleavages and Rearrangements Involving Oxygen Radicals and Cations.

The Reactions Of Ozone With Organic Compounds

Studies in the Polyoxyphenol Series: Viii. The Oxidation of Substances Related to Vanillin With Sodium Chlorite and Chlorine Dioxide

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