[Bis(aryloxyacetoxy)iodo]benzenes

Photomediated Controlled Radical Polymerization and Block Copolymerization of Vinylidene Fluoride

“…Although in the case of HVIC/R F –I mixtures, as seen above, the potential formation of CX 3 COOI (eq 3) can be neglected, rt reactions of I 2 with HVICs − ,,,, including IDAB, − ,− ,− IFAB, ,,− (ArOCH 2 COO) 2 IPh, CH 3 COOOH, − Hg­(OAc) 2 , AgOAc, − AgOPr, CF 3 COOAg, ,− (CF 3 COO) 2 Hg, etc., , as well as with R alk –I, , do proceed with the quantitative and fast formation of CX 3 COOI, even in the dark.…”

“…CX 3 COOI species are quite reactive reagents: CH 3 COOI was employed in electrophilic aromatic iodinations, − ,,,,,, iodoacetoxylations of double ,,,− , and triple bonds, and alcohol oxidations. ,, Similarly, CF 3 COOI adds to alkenes and is a stronger electrophilic iodination reagent, ,− ,, which, by contrast to CH 3 COOI, , may iodinate even the parent PhI. , Moreover, CX 3 COOI from (CX 3 COO) 2 PhI/R alk –I ,, or CH 3 COOOH/R alk –I , may oxidize R alk I to the corresponding CX 3 COOR alk . , …”

“…Consequently, RCOOI intermediates have found use in Hunsdieker-like photohalodecarboxylative reactions, or in halogenations with IDAB, IFAB, or their ligand-exchanged HVIC congeners in the presence of R–I ,, or I 2 . ,− ,− ,, However, they have never been employed in trifluoromethylations or polymerization reactions.…”

Hypervalent Iodine Chemistry: 25 Years of Development at the University of Thessaloniki

“…46 A study of the thermolytic behaviour of some [bis(aryloxyacetoxy)iodo]benzenes was performed either in the molten state or better in 1,4-dichorobenzene solution. 45 Two esters were the main products: the major 28 were the same as those obtained in reaction with iodine, while the minor were ArOCH 2 COOAr; the latter were probably the result of a nucleophilic attack from an intermediate ArOCH 2 COO -to the aromatic C of alkyl linked with O of the initial intermediate ArOCH 2 COOI + Ph.…”

“…44 A number of [bis(aryloxyacetoxy)iodo]benzenes, 25, reacted also with iodine affording initially the corresponding aryloxyacetyl hypoiodites 26, which underwent decarboxylation to aroxy-iodomethanes 27 and these gave eventually aryloxymethyl aryloxyacetates 28. 45 It should be noted that reaction of DIB and iodine with alcohols photochemically (Suarez reaction) leads to the generation of alkyl hypoiodites and then to alkoxy radicals which may undergo a plethora of useful transformations. 20…”