Über die Reaktion von Silbersalzen einbasischer Säuren mit Jod in Gegenwart von Cyclohexen, XXI. Mitteil.: Zur Kenntnis der Pseudohalogene

The Degradation Of Carboxylic Acid Salts By Means Of Halogen - The Hunsdiecker Reaction

“…Chemical evidence for the existence of acyl hypohalites is limited apparently to the observation of the oxidizing power of silver salt-halogen mixtures and the nature of the product from the treatment of an olefin with the supposed hypohalite. Bockemuller and Hoffmann (32) demonstrated the "positive" or oxidizing nature of the bromine ion in a bromine-silver butyrate mixture, and as others before and since (1,28,62,149,150,151,152,153,154,178), they showed that the acyl and halogen moieties add to the terminals of a carbon-carbon double bond.…”

Role of Lewis‐Base‐Coordinated Halogen(I) Intermediates in Organic Synthesis: The Journey from Unstable Intermediates to Versatile Reagents

“…(Acetato‐ O )iodine(I) – or acetyl hypoiodite or iodine(I) acetate – is a well‐known electrophilic iodinating agent. In 1932, Brickenbach and co‐workers proposed the formation of this intermediate when equimolar amounts of iodine and silver acetate (CH 3 COOAg) were added to diethyl ether at –80 °C and the filtrate was subsequently treated with cyclohexene, leading to the formation of trans ‐1‐acetoxy‐2‐iodocyclohexane . Later, Prevost and Woodward successfully employed this intermediate for stereoselective dihydroxylation of olefins …”

Organic Hypohalites.

“…Similarly, 1 Present address: Department of Chemistry, Israel Institute of Technology, Haifa, Schutzenberger obtained iodine triacetate through the oxidation of iodine in acetic anhydride by means of nitric acid. Acetyl hypoiodite has been formed in situ by the action of iodine on silver acetate, and the silver complexes of acyl hypoiodites have been studied extensively (10, 25,36,90,152,153,154,186,187,200). The addition of hypoiodites formed from the silver salts of polyfunctional acids to double bonds has also been studied (26).…”