Modular synthesis of triaroylbenzene-derived crownophanes
摘要:
An isomeric series of homologous crownophanes (i.e., macrocycles possessing structural features of crown ethers and cyclophanes) has been prepared via a concise and modular synthetic route. Macrocyclization is achieved in reasonable yield during the course of an enammone-triggered benzarmulation with bis(aryl ethynyl ketone) reaction partners. The crownophanes examined were active alkali cation binding agents in the gas phase, but failed to exhibit ionophoric properties in solution. On the basis of X-ray crystallographic analysis, it is concluded that the cyclophane framework of these macrocycles is too large and rigid to allow efficient interaction with the cations examined. (c) 2005 Elsevier Ltd. All rights reserved.
Modular synthesis of triaroylbenzene-derived crownophanes
作者:F. Christopher Pigge、Fatemeh Ghasedi、Angela V. Schmitt、Mayuri K. Dighe、Nigam P. Rath
DOI:10.1016/j.tet.2005.03.072
日期:2005.5
An isomeric series of homologous crownophanes (i.e., macrocycles possessing structural features of crown ethers and cyclophanes) has been prepared via a concise and modular synthetic route. Macrocyclization is achieved in reasonable yield during the course of an enammone-triggered benzarmulation with bis(aryl ethynyl ketone) reaction partners. The crownophanes examined were active alkali cation binding agents in the gas phase, but failed to exhibit ionophoric properties in solution. On the basis of X-ray crystallographic analysis, it is concluded that the cyclophane framework of these macrocycles is too large and rigid to allow efficient interaction with the cations examined. (c) 2005 Elsevier Ltd. All rights reserved.