70841-95-1Relevant academic research and scientific papers
Synthesis of different deuterated carboxylic acids from unsaturated acids promoted by samarium diiodide and D2O
Concellon, Jose M.,Rodriguez-Solla, Humberto
, p. 4493 - 4497 (2002)
An easy, and rapid reduction of the C=C bond of α,β-unsaturated acids by means of samarium diiodide in the presence of D2O provides an efficient method for synthesizing 2,3-dideuterio acids. Starting from alka-2,4-dienoic acids, (E)-α,δ-dideuterio-βγ-unsaturated acids are obtained, the new C=C bond being generated with complete diastereoselectivity. When H2O is used instead of D2O, saturated carboxylic acids and (E)-β,γ-unsaturated acids are isolated. A mechanism to explain each synthesis has been proposed.
Chemical-Reductant-Free Electrochemical Deuteration Reaction using Deuterium Oxide
Cheng, Xu,Li, Guigen,Liu, Ruoyu,Liu, Xu,Qiu, Jiaxing
supporting information, p. 13962 - 13967 (2020/06/10)
We report a method for the electrochemical deuteration of α,β-unsaturated carbonyl compounds under catalyst- and external-reductant-free conditions, with deuteration rates as high as 99 percent and yields up to 91 percent in 2 h. The use of graphite felt for both the cathode and the anode was key to ensuring chemoselectivity and high deuterium incorporation under neutral conditions without the need for an external reductant. This method has a number of advantages over previously reported deuteration reactions that use stoichiometric metallic reductants. Mechanistic experiments showed that O2 evolution at the anode not only eliminates the need for an external reductant but also regulates the pH of the reaction mixture, keeping it approximately neutral.
Conformational Analysis of 1,1,2-Trisubstituted Ethanes by PMR: Part I - 3-Aryl-2-methylpropanols
Somasekharan, K. N.,Kiefer, Edgar F.
, p. 29 - 37 (2007/10/02)
A self-consistent model for the conformational analysis of 1,1,2-trisubstituted ethanes is developed, based on the temperature dependence of vicinal proton-proton coupling constants.Synthesis of racemates of 2(R), 3(S)- and 2(S), 3(R)-2,3-dideutero-2-methyl-3-phenyl-1-propanols is accomplished using known reactions of well-defined stereochemistry.By comparing the PMR spectra of undeuterated and deuterated compounds, an unequivocal assignment of benzylic protons is made.Concentration and variable-temperature studies have revealed the existence of very weak intramolecular interaction in three alcohols, p-R-C6H4-CH2-CHMe-CH2-OH, where R = NO2, H and OMe.
