Silver(I) Benzoate

PhCO2Ag

[532-31-0]  · C7H5AgO2  · Silver(I) Benzoate  · (MW 228.99)

(nucleophile;2-4 Wolff rearrangement promoter1)

Solubility: sol water (0.262 g/100 mL); alkali (0.017 g/100 mL).

Form Supplied in: white powder and chunks.

Preparative Methods: prepared by equimolar reaction of solutions of Silver(I) Nitrate and sodium benzoate. The solid is collected and dried in vacuo.1

Handling, Storage, and Precautions: may be harmful by inhalation, ingestion, or skin absorption and may cause argyria. Store in a tightly closed container away from light in a cool, dry place. Incompatible with strong oxidizing agents. May discolor on exposure to light. Hazardous products from decomposition are carbon monoxide and carbon dioxide.

Introduction.

For additional information on silver benzoate and its reaction with iodine, see Iodine-Silver Benzoate.

Silver Benzoate as a Nucleophile.

The first use of silver benzoate was reported by Larock in which n-butyl iodide was reacted with silver benzoate in the presence of B(O2CPh)3 to give n-butyl benzoate in low yield (20%) (eq 1).2

It has been used in a reaction with 4,7-dichloro-3,8-diphenyl-1,2-diazocine to prepare 4-benzoyloxy-7-chloro-3,8-diphenyl- and 4,7-bis(benzoyloxy)-3,8-diphenyl-1,2-diazocine (eq 2).3

Isomides (Ar1 = p-MeOC6H4, Ph, p-BrC6H4, p-NO2C6H4; Ar2 = 2,4-(NO2)2C6H3) have been prepared by the reaction of the appropriately substituted silver benzoate with N-(2,4-dinitrophenyl)benzimidoyl chloride (eq 3).4

Wolff Rearrangement.

Newman and Bead developed a procedure for a Wolff rearrangement under mild, homogeneous reaction conditions. In an example of this protocol, diazoacetophenone is treated with a few drops of filtered silver benzoate in triethylamine (eq 4). Nitrogen evolution commences immediately. Silver benzoate is added in portions until gas evolution ceases. The product is obtained in 92% yield.1

Related Reagents.

Iodine-Silver Benzoate.


1. Newman, M. S.; Beal P. F., III JCS 1950, 72, 5163.
2. Larock, R. C. JOC 1974, 39, 3721.
3. Yogi, S.; Hokama, K.; Ueno, K.; Tsuge, O. BCJ 1986, 59, 1087.
4. Curtin, D. Y.; Miller, L. L. JACS 1967, 89, 637.

Bhadra Shelat & Brian A. Roden

Abbott Laboratories, North Chicago, IL, USA



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