Reaction of Cyclopropanamines with Hypochlorite

Journal Article (Journal Article)

Ethylene was formed in 65% yield when l-(l-piperidino)cyclopropanol, 6, was treated with hypochlorite. This observation raised the possibility that 1-aminocyclopropanecarboxylic acids (ACCs) could yield ethylene by a mechanism that involves (1) decarboxylation to a 1-aminocyclopropanol, followed by (2) a fragmentation of the carbinolamine to ethylene induced by a hypochlorite equivalent. Although this mechanism could be ruled out only for le, no evidence could be found for it in the reactions of other ACCs, la-f, with hypochlorite. The fact that lb-cis-2,3-d2yielded only ethylene-ds-l,2-d2is consistent with either the mechanism described above or a nitrenium ion mechanism. In the reaction of cyclopropanamines with neutral hypochlorite, ethylene is not the major product. From the primary and secondary amino acids la-c, a 3-hydroxypropanenitrile or propanamide, 2a-c, probably the product of a nucleophilic ring-opening step followed by decarboxylation, is formed. Similar products are formed from other cyclopropanamines: 2a from lg, 2d from lh, 2e and 2f from li, and lactone 5 from 1j. © 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

  • 1815 - 1820

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo00269a014

Citation Source

  • Scopus