Reaction of an Introverted Carboxylic Acid with Carbodiimide.
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.
Iwasawa
Tetsuo
T
The Skaggs Institute for Chemical Biology and Department of Chemistry The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037.
Wash
Paul
P
Gibson
Christoph
C
Rebek
Julius
J