A series of compounds possessing polyvalent iodine groups was prepared from onitroiodobenzene. Single crystal X-ray investigation revealed a strong interaction between iodine atom and one of the oxygen atoms of the nitro group. This interaction is strongest in trifluoroacetate of hydroxy(o-nitrophenyl)iodonium salt, which is formed from an iodosylarene and an acid being the first example of this new class of compounds. These compounds are also characterized by NMR-spectroscopy.
The Z-configured nitrones − O + N(Me)C(H)C 6 H 4 R 2p (R 2 = OMe (2a), Me (2b), NO 2 (2c)) react with the nitrile functionality of the closo-decaborate clusters [Bu n4 N][B 10 H 9 (NCR 1 )] (R 1 = Me (1a), Et (1b), Bu t (1c), Ph (1d)) in CHCl 3 solution under mild conditions (20−25 °C, 16−18 h) to afford the products of cycloaddition: viz., the borylated 2,3-dihydro-1,2,4-oxadiazoles. This reaction represents the first example of boron-mediated 1,3dipolar cycloaddition of allyl anion type dipoles, i.e. nitrones, to the nitrile group. Alteration of the lipophilic [Bu n4 N] + counterion with the hydrophilic Na + via the metathetical reaction with NaBPh 4 in 3a,b,e,f allows the modification of their hydrophilic−lipophilic properties and, consequently, solubility. Compounds 3a−j and 5a−d were characterized by high-resolution ESI-MS, IR, and 1 H, 13 C{ 1 H}, and 11 B{ 1 H} NMR spectroscopy. The structures of 3a,e,f were determined by single-crystal X-ray diffraction.
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