Decarboxylation of 1-Aminocyclopropanecarboxylic Acid and Its Derivatives

Journal Article (Journal Article)

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.

Full Text

Duke Authors

Cited Authors

  • Vaidyanathan, G; Wilson, JW

Published Date

  • April 1, 1989

Published In

Volume / Issue

  • 54 / 8

Start / End Page

  • 1810 - 1815

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo00269a013

Citation Source

  • Scopus