Department of Chemistry and Biochemistry, University of Minnesota-Duluth, Duluth, Minnesota 55812, USA.
J Org Chem. 2009 Nov 6;74(21):8444-7. doi: 10.1021/jo901638f.
New tosyl derivatives of 2-iodylaniline and 2-iodylphenol were prepared by the dimethyldioxirane oxidation of the corresponding 2-iodophenyltosylamides or 2-iodophenyl tosylate and isolated as stable, microcrystalline products. Single-crystal X-ray diffraction analysis of N-(2-iodylphenyl)-N,4-dimethylbenzenesulfonamide revealed pseudocyclic structure formed by intramolecular I...O interactions between the hypervalent iodine center and the sulfonyl oxygens in the tosyl group. This tosylamide has an excellent solubility in organic solvents and is a potentially useful hypervalent iodine oxidant.
新的 2-碘代苯胺和 2-碘代苯酚的对甲苯磺酰衍生物通过相应的 2-碘代苯甲酰胺或 2-碘代苯磺酸盐的二甲亚砜氧化制备，并作为稳定的微晶产物分离出来。N-(2-碘代苯基)-N,4-二甲基苯磺酰胺的单晶 X 射线衍射分析表明，通过高价碘中心与对甲苯磺酰基中磺酰氧基之间的分子内 I...O 相互作用形成了拟环结构。这种对甲苯磺酰胺在有机溶剂中具有极好的溶解性，是一种潜在有用的高价碘氧化剂。
