The Synthesis of α-Hydroxycarboxylic Acids by Aeration of Lithiated Carboxylic Acids in Tetrahydrofuran Solution

Moersch, G. W.; Zwiesler, M. L.

doi:10.1055/s-1971-21783

Cited by 27 publications

(10 citation statements)

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“…For those cases where it was considered conclusively established in the following manner. Sodium borohydride reduction of 3d gave an alcohol 5 which was different from that (6b) synthesized by the aerial oxidation (12) of the anion derived from 1-ethylthio-5-benzyl-1,3,4-thiadiazole 6a. 2-Ethylthio-5-benzoyl-1,3,4-thiadiazole 4d, the ketone isomeric with 3d, could be prepared from diazoacetophenone and ethyl chlorodithioformate in the presence of triethylamine, and reduction of this compound with sodium borohydride produced the alcohol 66. both the 1,2,3-and the 1,3,4-thiadiazoles 3b and 4b were present.…”

Section: ~mentioning

confidence: 79%

The reaction of certain α-diazocarbonyl compounds with thiophosgene and ethyl chlorodithioformate

Demaree¹,

Doria²,

Muchowski³

1977

Can. J. Chem.

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The reaction of thiophosgene with α-diazocarbonyl compounds produced mixtures of 1,2,3-and 1,3,4-thiadiazoles, in which the latter predominated, irrespective of whether the bis(α-diazoacyl)mercury derivatives or the free diazo compounds were used. In contrast, ethyl chlorodithioformate gave exclusively 1,3,4-thiadiazoles with α-diazocarbonyl compounds in the presence of triethylamine and only 1,2,3-thiadiazoles when the bis(α-diazoacyl)mercury derivatives were used.

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Section: ~mentioning

confidence: 79%

The reaction of certain α-diazocarbonyl compounds with thiophosgene and ethyl chlorodithioformate

Demaree¹,

Doria²,

Muchowski³

1977

Can. J. Chem.

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“…In similar fashion 0.95 mmol of LDA in 10 mL of THF was reacted with 180 mg (0.45 mmol) of ketal ester 2b (vide infra) in 2 mL of THF at -25 °C for 2 h. After addition of 0.103 g (1.1 mmol) of dimethyl disulfide and stirring for 30 min at -25 °C and 45 min at 0 °C, workup gave 191 mg (98%) of product: mp 167.5-168.5 °C (from hexane); IR (CC14) 3060, 1725, and 1250 cm"1; NMR (CC14) 5 5.18 (m, 1 H), 3.83 (s, 4 H), 3.67 (s, 3 H), singlets at 1.97, 1.40, 0.98, and 0.76 (3 H each) superimposed on m, 0.7-2.5 (20 H); mass spectrum m/e (rel %) 448 (4), 389 (1), 122 (6). 121 (7), 99 (100), 91 (12), and 55 (12). Caled for C26H40O4S: 448.2647.…”

Section: Methodsmentioning

confidence: 99%

New synthetic reactions. Oxidative decarboxylation of .alpha.-methylthiocarboxylic acids, new approach to acyl anion and ketene synthons

Trost¹,

Tamaru²

1977

J. Am. Chem. Soc.

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“…Identity of the alkylhalide was confirmed by liquid secondary ion mass spectrometry after derivatisation with triethylamine. A portion of the iodide (38 umol) was converted into 3-methyl-pentadecyl[l-14 C]nitrile in a phase-transfer catalyzed K I4 CN incorporation [16] similarly to the previously described synthesis of 2-methyl-[l-14 C]palmitic acid [3] and 3-methyl[l-14 C]heptadecanoic acid [17].…”

Section: -Hydroxy-3-methyl[l-' I C]hexadecanoyl-coamentioning

confidence: 99%

“…They first have to be shortened by one carbon atom via a-oxidation, a process until recently thought to yield CO2 and a 2-methyl-substituted fatty acid as the primary end products [1]. The 2-methyl-branched fatty acid is then degraded via |3-oxidation predominantly in the peroxisome [2][3][4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Formation of a 2‐methyl‐branched fatty aldehyde during peroxisomal α‐oxidation

et al. 1997

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In the final reaction of peroxisomal a-oxidation of 3-methyl-branched fatty acids a 2-hydroxy-3-methylacyl-CoA intermediate is cleaved to formyl-CoA and a hitherto unidentified product. The release of formyl-CoA suggests that the unidentified product may be a fatty aldehyde. When purified rat liver peroxisomes were incubated with 2-hydroxy-3-methylhexadecanoyl-CoA 2-methylpentadecanal was indeed formed. The production rates of formyl-CoA (measured as formate) and of the aldehyde were in the same range. While the production of formate remained unaltered in the presence of NAD+, the amount of 2-methylpentadecanal was decreased, which was accompanied by the formation of 2-methylpentadecanoic acid. These data indicate that (1) during a-oxidation the 2-hydroxy-3-methylacyl-CoA is cleaved to a 2-methyl-branched aldehyde and formyl-CoA and (2) liver peroxisomes are capable of converting this aldehyde to a 2-methyl-branched fatty acid. © 1997 Federation of European Biochemical Societies.

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The Synthesis of α-Hydroxycarboxylic Acids by Aeration of Lithiated Carboxylic Acids in Tetrahydrofuran Solution

Cited by 27 publications

References 0 publications

The reaction of certain α-diazocarbonyl compounds with thiophosgene and ethyl chlorodithioformate

The reaction of certain α-diazocarbonyl compounds with thiophosgene and ethyl chlorodithioformate

New synthetic reactions. Oxidative decarboxylation of .alpha.-methylthiocarboxylic acids, new approach to acyl anion and ketene synthons

Formation of a 2‐methyl‐branched fatty aldehyde during peroxisomal α‐oxidation

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