Tetrahedron Letters

Functionalization of carboxylic anhydrides at α-carbon with hypervalent iodine reagents: one-pot conversion of anhydrides to 2-sulfonyloxycarboxylate esters

JM Goff, MW Justik, GF Koser

Index: Goff, Jeffrey M.; Justik, Michael W.; Koser, Gerald F. Tetrahedron Letters, 2001 , vol. 42, # 33 p. 5597 - 5599

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Citation Number: 9

Abstract

In a typical experiment, a two-phase mixture of crystalline [hydroxy(tosyloxy)iodo]benzene (HTIB, 5.0 mmol) and butyric anhydride (24 mmol) was stirred and heated to ca. 100°C, during which time the mixture became homogeneous. After 20 min at 100–105°C, the solution was allowed to cool to 60°C. Methanol (25 mL) and p-TsOH·H 2 O (0.2 g) were introduced and the solution was heated under reflux for 4 hours and cooled to room temperature. After addition of CH ...