Unusually large reactivity differences in the transformation of cyclopropane lactones to 1-aminocyclopropane-1-phosphonic acids and their carboxylic acid analogues

Zsuzsa M. Jászay, György M. Keseru, György Clementis, Imre Petneházy, Katalin Kováts, László Toke

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Abstract

Starting from a cyclopropane lactone 5, the synthesis of a 1-aminocyclopropane-1-phosphonic acid derivative 11 is described. The considerable differences in the reactivity of the lactone ring opening in the case of a cyclopropane lactone substituted by a phosphonic acid ester 5 and their carboxylic acid ester analogue 2 toward ammonia or amines have been compared and interpreted by using the map of electrostatic potentials.

Original languageEnglish
Pages (from-to)90-96
Number of pages7
JournalHeteroatom Chemistry
Volume12
Issue number2
DOIs
Publication statusPublished - Apr 26 2001

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ASJC Scopus subject areas

  • Chemistry(all)

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