Related Experiment Video
Updated: Jun 23, 2026

Temperature-programmed Deoxygenation of Acetic Acid on Molybdenum Carbide Catalysts
Published on: February 7, 2017
Room-temperature reaction of carbon monoxide with a stable diarylgermylene
Xinping Wang1, Zhongliang Zhu, Yang Peng
1Department of Chemistry, University of California, Davis, One Shields Avenue, California 95616, USA.
Abstract:
Reactions of the heteroleptic diarylgermylenes GeAr(#)(Ar') (1) or GeAr(#) (Ar*-3,5-Pr(i)(2)) (2) (Ar(#) = C(6)H(3)-2,6-(C(6)H(2)-2,4,6-Me(3))(2); Ar' = C(6)H(3)-2,6-(C(6)H(3)-2,6-Pr(i)(2))(2); Ar*-3,5-Pr(i)(2) = C(6)H-2,6-(C(6)H(2)-2,4,6-Pr(i)(3))(2)-3,5-Pr(i)(2)) with carbon monoxide at room temperature gave alpha-germyloxy ketones via double CO insertion into the Ge-Ar' carbon bond in 1 and the Ge-Ar(#) bond in 2. The Ar(#)Ge-OCC(O)Ar' and 3,5-Pr(i)(2)Ar*Ge-O-CC(O)Ar(#) intermediates that are formed are unstable and rearrange via the insertion of the carbon of the GeOC moiety into a methyl-aryl or isopropyl carbon to form six-membered ring products.
Related Concept Videos
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
The carbonyl center is activated by...
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate
Acid Halides to Alcohols: Grignard Reaction
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
Acid Halides to Ketones: Gilman Reagent
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...

