Oxalyl chloride: A versatile reagent in organic synthesis

Abstract

(A) He and Chan showed a new class of odorless and non-volatile organosulfur compounds anchored on imidazolium ionic liquid, which can be used effectively for the oxidation of alcohols to aldehydes and ketones in the presence of oxalyl chloride1 under Swern oxidation conditions. 2 (Chemical Equation Presented) (B) Chen and workgroup reported a 1,1-cycloaddition of oxalyl chloride with 1,4-dilithio-1,3-dienes or zirconacyclopentadienes in the presence of CuCl and DMPU to afford cyclopentadienone derivatives in good yields.6 (Chemical Equation Presented) (C) Dede et al. showed a regioselective preparation of isoeletronic acids by cyclization of 1,3-bis(trimethylsilyloxy)alk-1-enes with oxalyl chloride in moderate yields.7 (Chemical Equation Presented) (D) Oh et al. reported a new and convenient method of generating phenyl isocyanates from anilines using oxalyl chloride. Acylation of a variety of substituted aniline hydrochlorides with oxalyl chloride affords the intermediate oxamic chlorides, which smoothly undergo thermal decomposition to the corresponding desired products.8 (Chemical Equation Presented) (E) Suau et al. showed that oxalyl chloride is a good promoter for bicyclization of a variety of biarylacetamides in the presence of SnCl4, which were used for the synthesis of aporphinoids.9 (Chemical Equation Presented) (F) Czifrák et al. reported a dehydration of per-O-benzoylated C-(1-azido-1-deoxy-α-D-glucopyranosyl)formamide by oxalyl chloride/DMF to give the corresponding nitrile in moderate yields.10 (Chemical Equation Presented) (G) Ehsan and Langer reported the use of oxalyl chloride in the synthesis of functionalized 3-hydroxymaleic anhydrides by cyclization of 1,1-bis(trimethylsilyloxy)ketene acetals.11 (Chemical Equation Presented). © Georg Thieme Verlag Stuttgart.