2-碘吡啶的制备、X 射线结构和反应性：可回收高价碘(V)试剂。

Preparation, X-ray structure, and reactivity of 2-iodylpyridines: recyclable hypervalent iodine(V) reagents.

机构信息

Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, Minnesota 55812, United States.

出版信息

J Org Chem. 2011 May 20;76(10):3812-9. doi: 10.1021/jo200163m. Epub 2011 Apr 14.

DOI:10.1021/jo200163m

Abstract

2-Iodylpyridine and four examples of 3-alkoxy-2-iodylpyridines were prepared by oxidation of the respective 2-iodopyridines with 3,3-dimethyldioxirane. Structures of 2-iodylpyridine, 2-iodyl-3-isopropoxypyridine, and 2-iodyl-3-propoxypyridine were established by single-crystal X-ray diffraction analysis. 2-Iodyl-3-propoxypyridine has moderate solubility in organic solvents (e.g., 1.1 mg/mL in acetonitrile) and can be used as a recyclable reagent for oxidation of sulfides and alcohols. The reduced form of this reagent, 2-iodo-3-propoxypyridine, can be effectively separated from the reaction mixture by treatment with diluted sulfuric acid and recovered from the acidic aqueous solution by adding aqueous sodium hydroxide.

摘要

2-碘吡啶和四个 3-烷氧基-2-碘吡啶的例子是通过 3,3-二甲基二氧杂环戊烷氧化各自的 2-碘吡啶得到的。2-碘吡啶、2-碘基-3-异丙氧基吡啶和 2-碘基-3-丙氧基吡啶的结构通过单晶 X 射线衍射分析确定。2-碘基-3-丙氧基吡啶在有机溶剂中有中等的溶解度（例如，在乙腈中的溶解度为 1.1mg/mL），可作为氧化硫化物和醇的可回收试剂。该试剂的还原形式，2-碘-3-丙氧基吡啶，可以通过用稀硫酸处理有效地从反应混合物中分离出来，并从酸性水溶液中通过加入氢氧化钠水溶液回收。