ChemInform Abstract: Unusually Large Reactivity Differences in the Transformation of Cyclopropane Lactones to 1‐Aminocyclopropane‐1‐phosphonic Acids and Their Carboxylic Acid Analogues.

Abstract

2001organo-phosphorus compounds organo-phosphorus compounds S 0080 -171Unusually Large Reactivity Differences in the Transformation of Cyclopropane Lactones to 1-Aminocyclopropane-1-phosphonic Acids and Their Carboxylic Acid Analogues. -Starting from a cyclopropane lactone (I), the synthesis of aminocyclopropane-1-phosphonic acid derivatives (VIII)/(IX) 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 (I) and their carboxylic acid ester analogue toward ammonia are compared and interpreted by using the map of electrostatic potentials. -(JASZAY, ZSUZSA M.; KESERU, GYOERGY M.; CLEMENTIS,