Acid-catalyzed hydrogen-deuterium exchange in beta-pyrrolic positions of calix[4]pyrrole at room temperature

作者：He, Ying-Chun; Pan, Ji-Gang^*; Liu, Dian-Sheng

来源：Tetrahedron Letters, 2016, 57(29): 3133-3136.

DOI：10.1016/j.tetlet.2016.06.015

• Calix[4]pyrrole
• beta-Pyrrolic positions
• Hydrogen-deuterium exchange
• Crystal structure

Calix[4]pyrrole was found to be high deuterium incorporation and easy-to-make hydrogen-deuterium exchange in beta-pyrrolic positions with the 98% sulphuric acid as catalyst in D2O/CH3CN-D2O/CHCl3-D2O. Compounds 2a-d were obtained by acid-catalyzed hydrogen-deuterium exchange in beta-pyrrolic positions of calix[4]pyrroles 1a-d, respectively. Deuterium labeling at the pyrrole-beta-position for compounds 1b and 1c can be achieved with nearly 100% incorporation in D2O-H2SO4 and CH3CN-D2O-H2SO4 systems, and deuterium labelling at the pyrrole-p-position for la and Id is more than 90% in CHCl3-D2O-H2SO4.

• 出版日期2016-7-20
• 单位中国科学院长春应用化学研究所; 山西大学