145351-38-8Relevant academic research and scientific papers
One-step facile synthesis of deuterium labeled aldehydes from tertiary amides using Cp2Zr(D)Cl
Spletstoser, Jared T.,White, Jonathan M.,Georg, Gunda I.
, p. 2787 - 2789 (2004)
The synthesis of deuterium labeled aldehydes was accomplished in an expedient and facile manner through the reduction of amides using commercially available Cp2Zr(D)Cl. The reactions proceeded rapidly (ca. 15min) and in high yields (70-99%).
Selective oxidation of alcohol-d1to aldehyde-d1using MnO2
Kitsuwa, Kohei,Kumadaki, Katsushi,Nakayama, Atsushi,Okamura, Hironori,Ozawa, Keita,Shinada, Tetsuro,Tamura, Yusaku,Yamamoto, Yuki,Yasuno, Yoko
, p. 28530 - 28534 (2021/09/22)
The selective oxidation of alcohol-d1to prepare aldehyde-d1was newly developed by means of NaBD4reduction/activated MnO2oxidation. Various aldehyde-d1derivatives including aromatic and unsaturated ald
Mild and selective hydrozirconation of amides to aldehydes using Cp 2Zr(H)Cl: Scope and mechanistic insight
Spletstoser, Jared T.,White, Jonathan M.,Tunoori, Ashok Rao,Georg, Gunda I.
, p. 3408 - 3419 (2007/10/03)
An investigation of the use of Cp2Zr(H)Cl (Schwartz's reagent) to reduce a variety of amides to the corresponding aldehydes under very mild reaction conditions and in high yields is reported. A range of tertiary amides, including Weinreb's amides, can be converted directly to the corresponding aldehydes with remarkable chemoselectivity. Primary and secondary amides proved to be viable substrates for reduction as well, although the yields were somewhat diminished as compared to the corresponding tertiary amides. Results from NMR experiments suggested the presence of a stable, 18-electron zirconacycle intermediate that presumably affords the aldehyde upon water or silica gel workup. A series of competition experiments revealed a preference of the reagent for substrates in which the lone pair of the nitrogen is electron releasing and thus more delocalized across the amide bond by resonance. This trend accounts for the observed excellent selectivity for tertiary amides versus esters. Experiments regarding the solvent dependence of the reaction suggested a kinetic profile similar to that postulated for the hydrozirconation of alkenes and alkynes. Addition of p-anisidine to the reaction intermediate resulted in the formation of the corresponding imine mimicking the addition of water that forms the aldehyde.
α-(METHYLTHIO)BENZYL SULFONES AS SYNTHETIC INTERMEDIATES. PART V. SYNTHESES OF SOME o- AND m-SUBSTITUTED 1-DEUTERIOBENZALDEHYDES
Wladislaw, B.,Marzorati, L.,Ebeling, G.
, p. 25 - 28 (2007/10/02)
o- and m-Substituted α-methylthiobenzyl sulfones incorporate deuterium when treated with a base and deuterium oxide.The resulting deuterated sulfones, by thermal decomposition, afford o- and m-substituted 1-deuteriobenzaldehydes in good yields and high is
