2206-26-0Relevant articles and documents
Reaction of 3-Chloro-3-methyldiazirines with Hydrogen Atoms
Burkholder, C. D.,Jones, W. E.,Wasson, J. S.,Liu, M. T. H.
, p. 2847 - 2848 (1980)
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Leitch
, p. 345 (1957)
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Organocatalytic Deuteration Induced by the Dynamic Covalent Interaction of Imidazolium Cations with Ketones
Ananikov, Valentine P.,Galkin, Konstantin I.,Gordeev, Evgeniy G.
supporting information, p. 1368 - 1378 (2021/01/18)
In this article, we suggest a new organocatalytic approach based on the dynamic covalent interaction of imidazolium cations with ketones. A reaction of N-alkyl imidazolium salts with acetone-d6 in the presence of oxygenated bases generates a dynamic organocatalytic system with a mixture of protonated carbene/ketone adducts acting as H/D exchange catalysts. The developed methodology of the pH-dependent deuteration showed high selectivity of labeling and good chiral functional group tolerance. Here we report a unique methodology for efficient metal-free deuteration, which enables labeling of various types of α-acidic compounds without trace metal contamination. (Figure presented.).
Ruthenium-catalyzed selective α-deuteration of aliphatic nitriles using D2O
Krishnakumar, Varadhan,Gunanathan, Chidambaram
supporting information, p. 8705 - 8708 (2018/08/07)
Selective catalytic α-deuteration of aliphatic nitriles using deuterium oxide as a deuterium source is reported. A PNP-ruthenium pincer complex catalyzed the α-deuteration of aliphatic nitriles including acetonitrile. Efficient deuteration occurred with a low catalyst load (0.2 to 0.5 mol%) and under mild conditions. A [2+2] cycloadduct formation from nitrile functionality and a deprotonated catalytic intermediate, followed by an imine-enamine tautomerization and a H/D exchange between the enamine intermediate and deuterium oxide leading to the selective deuteration at the α-position of the nitrile, is proposed as a plausible reaction mechanism.
(2+2)-Cycloreversionsprodukte aus 2-(Methylazo)propen?
Remmler, Matthias,Ondruschka, Bernd,Ziegler, Ulrich,Zimmermann, Gerhard
, p. 396 - 397 (2007/10/02)
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