N,N′‐Diiodo‐N,N′‐1,2‐ethanediylbis(p‐toluenesulfonamide) as a Reagent for Conversion of Aldehydes to Methyl Esters.

Abstract

Carboxylic acid esters Q 0530 N,N'-Diiodo-N,N'-1,2-ethanediylbis(p-toluenesulfonamide) as a Reagent forConversion of Aldehydes to Methyl Esters. -The proposed mechanism for the conversion of aldehydes (I) to esters (III) involves the oxidation of the initially formed methyl hemiacetal by the title reagent to the corresponding hypoiodite and subsequent elimination of hydrogen iodide. Double bonds as well as functional groups like chloro, methoxy and alkyl are inert to this reagent; by-products are not observed. Following advantages of the title reagent are remarkable i) easy preparation, ii) stability (six months under atmospheric conditions), iii) recovery/reuseability without loss of yield.-(GHORBANI-VAGHEI*, R.; SHAHBAZEE, E.; VEISI, H.; Mendeleev Commun. 2005, 5, 207-208; Dep. Chem., Coll. Sci., Univ. Bu-Ali Sina, Hamadan 65174, Iran; Eng.) -H. Hoennerscheid 03-098