ortho-Phosphoryl stabilized hypervalent iodosyl- and iodyl-benzene reagents

Chemistry of Polyvalent Iodine

“…92 Single crystal X-ray analysis of compound 511 has shown a close contact of the phosphoryl oxygen atom and the iodine(V) atom with a distance of 2.612 Å, which is significantly shorter than the I•••O distance of 3.291 Å determined for the unoxidized aryliodide 510 92…”

“…It is assumed that the initial oxidation of ArI usually leads to iodosylarenes, ArIO, which then slowly disproportionate to ArI and ArIO 2 upon gentle heating, or even at room temperature 92,256,939. The most common oxidizing reagents that are used for the preparation of iodylarenes from iodoarenes include sodium hypochlorite, sodium periodate, dimethyldioxirane, and oxone.…”

N‐Heterocycle‐Stabilized Iodanes: From Structure to Reactivity

“…Extensive secondary intermolecular I···O interactions of unstabilized iodanesp roduced highlyi nsoluble and thermally labile polymeric networks. [9,10] Besidesf ormationo ff ive-membered cyclic hypervalent iodine heterocycless uch as benziodoxoles or benziodazoles, [11,12] pseudocycles can be generated through (capto)dative bonding interactionst hrough the covalent attachment of Lewis basic units.I np ioneering examples, Protasiewicza nd coworkers employed ortho-sulfonyl-and phosphoryl-groupsini odosylarenes 1 [13][14][15] and 2 [16] as covalently boundc oordinating and stabilizing units ( Figure 1A). The pseudocyclicb enziodoxole triflates and tosylates 3 werep ublished by Zhdankin and co-workers.…”

Palladium‐catalysed PC bond forming reactions between diphenylphosphine and ortho‐substituted aryl bromides

“…The solvent was removed and the product was oxidized with an excess of H 2 O 2 before purification by column chromatography, (ethyl acetate–hexane, 95:5; 348 mg; 0.64 mmol; 72%). This compound has been previously reported in the literature 11…”