2-Iodosylphenylacetic acid

The first six-membered iodine(III) heterocycle, the cyclic tautomer of 2-iodosylphenylacetic acid, 221, was reported in 1963 by Leffler and coauthors [342]. This compound was synthesized by chlorination of 2-iodophenylacetic acid (220) followed by hydrolysis of the initially formed, unstable 2-(dichloroiodo)phenylacetic acid (Scheme 2.67). Compound 221 is stable at room temperature but decomposes in solution at 80-100 °C the proposed cyclic structure 221 is in agreement with its relatively low acidity (pXa = 7.45) [342]. 8-Iodosyl-l-naphthoic acid (222) was prepared by the peracetic oxidation of 8-iodo-1-naphthoic acid [343]. Anions of 2-iodosylphenylacetic acid (221) [328] and 222 [343] have a moderate reactivity in the cleavage of phosphate esters in aqueous micellar solution. The chiral, enantiomerically pure substituted 2-iodosylphenylacetic acid derivatives 223 and 224 were synthesized from the corresponding aryl iodides by oxidation with dimethyldioxirane [344]. 

Preparation of the first example of a six-membered iodine(III) heterocycle, the cyclic tautomer of 2-iodosylphenylacetic acid 192, was reported in 1963 by Leffler and coauthors (1962JA3443). This compound was synthesized by chlorination of 2-iodophenylacetic acid 191 followed by hydrolysis of the initially formed, unstable 2-(dichloroiodo)phenylacetic acid (Scheme 41). Compound 192 is stable at room temperature but decomposes in solution at 80—100 °C the proposed cyclic structure 192 is in agreement... 

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