Hypervalent iodine induced nucleophilic additions to alkenes: Synthesis of 1,2-diperchlorates

Vicinal Difunctionalization of Alkenes with Iodine(III) Reagents and Catalysts

“…Finally, various protocols have been developed for the dioxygenation of alkenes in the presence of hypervalent iodineA C H T U N G T R E N N U N G (III) reagents using oxygen nucleophiles that may be provided by the hypervalent iodine itself. [15][16][17] Examples include the reagents 16-18. The corresponding reactions are again represented for cyclohexene 2 as a substrate (Scheme 4).…”

New oxidative transformations of alkenes and alkynes under the action of diacetoxyiodobenzene

“…For instance, the oxidation of (E) stilbene (13) with the DIB-H 2 SO 4 system was nonselective and gave a mixture of compounds 3c, 8c, 9c, and 10b-12b (see Table 1, entries [13][14][15]. This fact is explained by the poor solubil ity and low nucleophilicity of (E) stilbene.…”

The Achmatowicz Rearrangement – Oxidative Ring Expansion of Furfuryl Alcohols

“…Here, Piancatelli and co-workers developed a rather general methodology to perform oxidative nucleophilic additions to olefins using diacetoxyiodobenzene as electron acceptor, including the dimethoxylation of furan and 2,5-dimethylfuran. [90][91][92][93] Like in the case of brominative furan cleavage, in aqueous media, (radical) cation trapping by water leads to the formation of labile hemiacetals that undergo ring expansion in the presence of adjacent nucleophilic groups. Hence, during the treatment of furfuryl alcohols with diacetoxyiodobenzene and magnesium perchlorate in aqueous acetonitrile, smooth oxidative ring enlargement was observed and the pyranones were obtained in good to excellent yields (Scheme 27…”