Efficient cyclodehydration of dicarboxylic acids with oxalyl chloride. Issue 32 (9th August 2017)

• Record Type: Journal Article
• Authors: Kantin, Grigory; Chupakhin, Evgeny; Dar'in, Dmitry; Krasavin, Mikhail
• Is Part Of: Tetrahedron letters. Volume 58:Issue 32(2017)
• Page Start: 3160
• Page End: 3163
• Publication Date: 2017-08-09
• Subjects: Dicarboxylic acid cyclodehydration -- Cyclic anhydride -- Oxalyl chloride -- Oligomerization side-reaction -- N, N-Dimethyl formamide catalyst; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.06.089
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Oxalyl chloride promotes cyclodehydration of dicarboxylic acids. DMF accelerates the reaction, suggesting intermediacy of a monoacyl chloride. The method can be applied to a wide range of structurally diverse carboxylic acids. Abstract: Literature examples illustrating the use of oxalyl chloride to prepare dicarboxylic acid anhydrides are surprisingly limited. At the same time, we have discovered a method involving the use of this readily available reagent which allowed the preparation of novel cyclic anhydrides where other, more conventional, methods had failed. Herein, we demonstrate that the method is applicable to a wide diversity of substrates, delivers good to excellent yields of cyclic anhydrides without chromatographic purification and can be considered a synthetic tool of choice whenever dicarboxylic acid cyclodehydration is required.