501037-03-2

Upstream product

• 768-93-4 1-iodoadamantane 
• 501037-00-9 1-benzenesulfonyl-2,2,2-trifluoro-ethanone O-benzyl-oxime 
• 828-51-3 1-Adamantanecarboxylic acid 
• 501036-99-3 N-benzyloxy-2,2,2-trifluoro-thioacetimidic acid phenyl ester 
• 501036-98-2 N-(benzyloxy)-2,2,2-trifluoroacetimidoyl chloride 
• 622-33-3 N-benzyloxyamine 

Relevant academic research and scientific papers

Silver-Catalyzed Radical Transformation of Aliphatic Carboxylic Acids to Oxime Ethers

Oximes and oxime ethers are privileged building blocks and can be conveniently converted to ketones, amines, hydroxylamines, and nitriles. We describe the catalytic decarboxylation of aliphatic carboxylic acids to oxime ethers. With AgNO3 as the catalyst, valuable oxime ethers bearing various substituents could be easily obtained. The broad substrate scope, easy accessibility of aliphatic carboxylic acids, and mild reaction conditions make this strategy immediately applicable to the synthesis, late-stage functionalization, and modification of biologically active compounds. Experimental studies show the reaction undergoes a radical process.

Radical-mediated synthesis of trifluoroethyl amines and trifluoromethyl ketones from alkyl iodides

Radical reaction of alkyl iodides with trifluoromethyl phenylsulfonyl oxime ether 10 and hexamethylditin at 300 nm in benzene afforded the corresponding trifluoromethyl oxime ethers 11 in high yields, which were reduced into the 2,2,2-trifluoroethyl amines with lithium aluminium hydride. The trifluoroethyl amines could be converted into the corresponding trifluoromethyl ketones by treatment with NBS and DBU.