Dehydroabietic Acid Derivatives. An Unusual α-Oxidation of a Ketone<sup>1</sup>

Wenkert, Ernest; Carney, Richard W. J.; Kaneko, Chikara

doi:10.1021/ja01482a033

Cited by 32 publications

(8 citation statements)

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“…Chromic acid oxidation (1,13,14) of dehydroabietane (Ie) yielded a mixture of ketoacetate Va and diketone Vb. Wolff-Kishner reduction and simultaneous hydrolysis of the former produced the carbinol Ig, whose alternate synthesis from the second oxidation product (Vb) proceeded as follows.…”

Section: Dehydroabietane Derzvativesmentioning

confidence: 99%

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Derivatives of Dehydroabietic and Podocarpic Acids

Wenkert¹,

Beak²,

Carney³

et al. 1963

Can. J. Chem.

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The lithium a l u~n i n u~n hydride reduction of nitriles in the aroxnatic resin acid series to aldimines and the conversion of the products to other derivatives are described. The effect of the stereochemistry of the nitriles on the rate of reduction is noted. The transformation of dehydroabietane into a dehydro product is indicated. The syntheses of a desoxydecarboxy-5,6-dehydro-7-keto derivative of podocarpic acid and its optical antipode are discussed. The stereochemistry of hydrogenation of 5,6-dehydro derivatives of podocarpic acid is reported. The effect of a 7-keto group on the rate of hydrolysis of methyl esters of aromatic resin acids is illustrated. The reactions of 6-bromo-7-keto derivatives of methyl podocarpate with bases are portrayed.

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Section: Dehydroabietane Derzvativesmentioning

confidence: 99%

“…Compounds IVe and Vd were exposed to selenium dioxide oxidation, a reaction which has been shown recently to convert 7-keto compounds to their 5,G-dehydro derivatives (1,17 For personal use only.…”

Section: Dehydroabietane Derzvativesmentioning

confidence: 99%

Derivatives of Dehydroabietic and Podocarpic Acids

Wenkert¹,

Beak²,

Carney³

et al. 1963

Can. J. Chem.

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“…After elution three spots were isolated ; the higher one was identiÐed as compound 2 (343 mg, 67%), the middle one as compound 4 (36 mg, 6%) and the lower one as compound 3 (20 mg, 4%). (12), 213 (29), 199 (20), 187 (37), 171 (15), 159 (19), 145 (15), 128 (20), 115 (23), 91 (16), 83 (18), 77 (13), 69 (15), 59 (41), 55 (23), 53 (13).…”

Section: Synthesesmentioning

confidence: 99%

“…(300. (15), 213 (47), 202 (32), 199 (33), 187 (66), 171 (16), 165 (13), 157 (12), 152 (11), 141 (18), 128 (30), 115 (31), 101 (14), 95 (19), 91 (13), 77 (13), 69 (18) (16), 199 (15), 185 (16), 159 (19), 55 (11).…”

Section: Yellow Oil ;mentioning

confidence: 99%

Synthesis and structural characterisation of ring B oxidised derivatives of dehydroabietic acid

et al. 2001

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“…When dehydroabietic acid is oxidized with chromic acid, the reaction takes place at the α position. 10 Resin acids have conjugated double bonds, their chemical properties are active, and they easily oxidize in air or oxygen. Hydroperoxides easily form when rosin acid is oxidized, and they have an allergic reaction to the human body.…”

Section: ■ Introductionmentioning

confidence: 99%

Thermal Stability Evaluation of Resin Acids and Rosin Modified Resins

Liu

Saburi

et al. 2020

ACS Omega

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Rosin is a sustainable resource, which is mainly composed of resin acid. Rosin-modified resin is widely used in adhesives, inks, coatings, and other fields, and its stability is very important for the production, storage, and use of products. Thermal stability and reactivity of three resin acids (levopimaric acid, neoabietic acid, and dehydroabietic acid) and four rosin-modified resins were studied using an accelerating rate calorimeter (ARC). They are stable, and exothermic reactions do not occur even when they were heated to 200 °C under a nitrogen atmosphere, but they are unstable under an oxygen atmosphere. The mechanism of the oxidation reaction process was found: first, resin acids absorb oxygen, and then an exothermic oxidation occurs. The initial exothermic temperature (T 0) of levopimaric acid, neoabietic acid, and dehydroabietic acid are 354.01, 353.83, and 398.20 K, the initial oxidation kinetics shows a second-order reaction, and the activation energies (E a) are 42.90, 58.05, and 46.60 kJ/mol, respectively. Peroxide concentration of three resin acids were determined by iodometry. The T 0 values of hydrogenated rosin, disproportionated rosin, hydrogenated rosin glyceride, and hydrogenated rosin pentaerythritol ester, the four rosin-modified resin, are 353.71, 348.32, 412.85, and 412.44 K. Levopimaric acid and neoabietic acid have higher oxidative reactivity and easily undergoes an oxidation reaction at lower temperature. Rosin-modified resins are stable and find it difficult to undergo oxidation reactions.

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Dehydroabietic Acid Derivatives. An Unusual α-Oxidation of a Ketone¹

Cited by 32 publications

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Derivatives of Dehydroabietic and Podocarpic Acids

Derivatives of Dehydroabietic and Podocarpic Acids

Synthesis and structural characterisation of ring B oxidised derivatives of dehydroabietic acid

Thermal Stability Evaluation of Resin Acids and Rosin Modified Resins

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Dehydroabietic Acid Derivatives. An Unusual α-Oxidation of a Ketone1

Cited by 32 publications

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Derivatives of Dehydroabietic and Podocarpic Acids

Derivatives of Dehydroabietic and Podocarpic Acids

Synthesis and structural characterisation of ring B oxidised derivatives of dehydroabietic acid

Thermal Stability Evaluation of Resin Acids and Rosin Modified Resins

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Product

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Dehydroabietic Acid Derivatives. An Unusual α-Oxidation of a Ketone¹