TY - JOUR

T1 - Efficient cyclodehydration of dicarboxylic acids with oxalyl chloride

AU - Kantin, Grigory

AU - Chupakhin, Evgeny

AU - Dar'in, Dmitry

AU - Krasavin, Mikhail

PY - 2017/1/1

Y1 - 2017/1/1

N2 - 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.

AB - 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.

KW - Cyclic anhydride

KW - Dicarboxylic acid cyclodehydration

KW - N,N-Dimethyl formamide catalyst

KW - Oligomerization side-reaction

KW - Oxalyl chloride

UR - http://www.scopus.com/inward/record.url?scp=85021953813&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2017.06.089

DO - 10.1016/j.tetlet.2017.06.089

M3 - Article

AN - SCOPUS:85021953813

VL - 58

SP - 3160

EP - 3163

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 32

ER -