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

✍ Scribed by Zsuzsa M. Jászay; György M. Keserű; György Clementis; Imre Petneházy; Katalin Kováts; László Tőke

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 194 KB
• Volume: 12
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.5

✦ Synopsis

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. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:90–96, 2001