Exchange reactions of carboxylic acid salts. Facile preparation of .alpha.-deuteriocarboxylic acids

Atkinson, J. G.; Csakvary, Jeno J.; Herbert, George; Stuart, R. S.

doi:10.1021/ja01004a054

Cited by 91 publications

(21 citation statements)

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“…The early literature 20 of deuterium chemistry features a large number of papers on the exchange behaviour H/D of carboxylic acids. Kinetic studies were most common, followed by combustion analysis, and neither enabled exchange to be definitively located in such compounds.…”

Section: Resultsmentioning

confidence: 99%

An expeditious procedure for the synthesis of isotopically labelled fatty acids: preparation of 2,2-d2-nonadecanoic acid

Guaragna

Nisco

Pedatella

et al. 2006

J Label Compd Radiopharm

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SummaryWe describe a new synthetic path for the preparation of isotopically labelled saturated odd-numbered fatty acids by a homologation procedure for the direct conversion of carboxylic acids into their 2,2-dideuterated homologues. This process can be used to obtain both odd-and even-numbered 2,2-dideuterated fatty acids starting from carboxylic acids. Furthermore, the reiteration of this process can also be used for the synthesis of polydeuterated fatty acids in which the heavy atoms are placed on adjacent carbon atoms or differently arranged in the molecule.

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Section: Resultsmentioning

confidence: 99%

An expeditious procedure for the synthesis of isotopically labelled fatty acids: preparation of 2,2-d2-nonadecanoic acid

Guaragna

Nisco

Pedatella

et al. 2006

J Label Compd Radiopharm

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“…The starting diolefinic compounds 8 and 8-d were prepared according to methods described in the literature (8,9). The acetonitrile (from Aldrich) was used without further purification.…”

Section: Resultsmentioning

confidence: 99%

Electrochemical oxidation of trifluoroacetic acid anion. V. Formation of bis(trifluoromethyl) alicyclic compounds from activated dienes

Renaud¹,

Stephens²,

Bérubé³

1982

Can. J. Chem.

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The electrochemical oxidation of trifluoroacetate anion in the presence of activated dienes, ROOCCH=CH(CH2)nCH=CHCOOR, gave bis(trifluoromethyl) alicyclic products. The ring size of the products was determined by comparing the fluorine nuclear magnetic resonance spectra of the protonated with the corresponding α,α′-dideuterated compounds. The results can be explained by an intramolecular radical addition and by an intramolecular coupling of a biradical intermediate.

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“…YO. Two diacids (n = 12 and 16) were also specifically u-deuteriated by exchange with D 2 0 but without the platinum on carbon catalyst [21].…”

Section: Methodsmentioning

confidence: 99%

Deuterium NMR of perdeuteriated di and monoacids dissolved in the lyomesophases of dipotassium hexadecanedioate

Gutman¹,

Luz²,

Loewenstein³

et al. 1990

Liquid Crystals

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The behaviour of a,w-diacid and a-monoacid guest molecules (with carbon atoms ranging between 6 to 22) in the lamellar and hexagonal mesophases of dipotassium thapsate (KOOC(CH,),,COOK)-water mixtures have been investigated, using deuterium NMR spectroscopy. Addition of short diacids to either the lamellar or hexagonal phases results in phase separation and essentially no incorporation into the mesophase structure. The deuterium spectra of the guest molecules exhibit characteristic patterns which are qualitatively interpreted in terms of their ordering properties. In no case were separate signals observed due to folded diacid guest molecules which have their carboxyl groups on the same side of the interface.

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Exchange reactions of carboxylic acid salts. Facile preparation of .alpha.-deuteriocarboxylic acids

Cited by 91 publications

References 1 publication

An expeditious procedure for the synthesis of isotopically labelled fatty acids: preparation of 2,2-d2-nonadecanoic acid

An expeditious procedure for the synthesis of isotopically labelled fatty acids: preparation of 2,2-d2-nonadecanoic acid

Electrochemical oxidation of trifluoroacetic acid anion. V. Formation of bis(trifluoromethyl) alicyclic compounds from activated dienes

Deuterium NMR of perdeuteriated di and monoacids dissolved in the lyomesophases of dipotassium hexadecanedioate

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