Decarboxylation of 1-Aminocyclopropanecarboxylic Acid and Its Derivatives

The question of whether the title compounds could be decarboxylated to cyclopropanone derivatives was answered in the affirmative by the following observations. (1) Compound 11a was decarboxylated by 1,2,3-indantrione in acetonitrile, benzene, or methanol. The initially formed intermediate could be trapped by N-phenylmaleimide (to form 3), by diethyl azodicarboxylate (to form an unstable adduct), by ninhydrin itself (to form 5) or by a proton (in methanol, to form 8). (2) Compound 11d was decarboxylated by phenylbis(trif!uoroacetato-0)iodine to yield carbinolamine 12d. cis-2,3-Dideuterio-lld yielded cis-2,3-dideuterio-12d under the same conditions. (3) ACC was decarboxylated by phenanthroquinone to yield oxazole 9, probably by way of oxazoline 10. © 1989, American Chemical Society. All rights reserved.

Duke Scholars

Author Ganesan Vaidyanathan Radiology