Cadmium compounds ketones from

D. A. Shirley, The Synthesis of Ketones from Acidhalides and Organometallic Compounds of Magnesium, Zinc and Cadmium, Organic Rcaktions, Vol. VIII, 28 (1954). 

Because of the toxicity of cadmium compounds two alternative methods for the preparation of ketones from carboxylic acid derivatives are worthy of attention. The first involves the reaction of organocopper reagents [formed from copper(i) iodide and an alkyllithium] with a carboxylic acid chloride.12 7a,b... 

D. A. Shirley, The synthesis of ketones from acid halides and organometallic compounds of magnesium, zinc, and cadmium, Org. React. 1954, 8, 28-58. 

You met organocopper reagents in Chapter 10 where you saw that they did conjugate additions to a,p-unsaturated carbonyl compounds. Other metals, such as cadmium or manganese, can also be used to make ketones from acid chlorides. 

The synthesis of ketones from acid halides and organometallic compounds of magnesium, zinc and cadmium... 

O. R. 1-9, C. R. Hauser and B. E. Hudson, Jr., The Acctoacetic Ester Condensation and Related Reactions lV-4, S. M. McElvain, The Acyloins 11-4, W. S. Johnson, The Formation of Cyclic Ketones by Intramolecular Acylation VIII-2, D. A. Shirley, The Synthesis of Ketones from Acid Chlorides and Organometallic Compounds of Magnesium, Zinc, and Cadmium. ... 

The mercury and cadmium compounds are much less reactive than the lithium or magnesium systems, and are therefore useful for certain reactions where selectivity is important. The most widely applied example of this strategy is the preparation of ketones from acid chlorides and cadmium reagents. The cadmium reagent is useful because it is too unreactive to add to the product ketone, and the reaction therefore stops at the ketone stage. Scheme 5.5 lists some examples of this reaction. At... 

Codeposition of silver vapor with perfluoroalkyl iodides at -196 °C provides an alternative route to nonsolvated primary perfluoroalkylsilvers [272] Phosphine complexes of trifluaromethylsilver are formed from the reaction of trimethyl-phosphme, silver acetate, and bis(trifluoromethyl)cadmium glyme [755] The per-fluoroalkylsilver compounds react with halogens [270], carbon dioxide [274], allyl halides [270, 274], mineral acids and water [275], and nitrosyl chloride [276] to give the expected products Oxidation with dioxygen gives ketones [270] or acyl halides [270] Sulfur reacts via insertion of sulfur into the carbon-silver bond [270] (equation 188)... 

Grignard reagents derived from aryl bromides are readily prepared and may be converted into organocadmium compounds by treatment with cadmium chloride (cf. Section 5.8.4, p. 616). Reaction of an organocadmium with a carboxylic acid chloride constitutes a convenient synthesis of aryl alkyl ketones. 

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