Reaction of an Introverted Carboxylic Acid with Carbodiimide

Tetrahedron. 2007 Jul 9;63(28):6506-6511. doi: 10.1016/j.tet.2007.03.075.

Abstract

The reaction of carboxylic acids with carbodiimides is reviewed, and an "introverted" carboxylic acid is proposed as a means of trapping reactive intermediates along the reaction pathway. The introverted acid is a cavitand with the carboxylic function directed toward the floor of the cavity. Its reaction with diisopropyl carboodiimide gives a covalent adduct that is either the elusive O-acylisourea or the commonly encountered N-acylurea.