Zwitterionic borane adducts of N-heterocyclic carbenes from mesomeric betaines of uracil

作者:Zhang Jiaxi; Pidlypnyi Nazar; Nieger Martin; Namyslo Jan C; Schmidt Andreas*
来源:Organic and Biomolecular Chemistry, 2014, 12(17): 2737-2744.
DOI:10.1039/c3ob42462f

摘要

We prepared a series of imidazolium-substituted uracil-anions which are members of the class of cross-conjugated heterocyclic mesomeric betaines. They are in tautomeric equilibrium with their N-heterocyclic carbenes, uracil-6-yl-imidazol-2-ylidenes. These carbenes can be trapped by reaction with sulfur, selenium, as well as by triethylborane and triphenylborane, respectively. The latter trapping reaction yielded the first representatives of a new heterocyclic zwitterionic ring system, imidazo[ 2',1':3,4][1,4,2]diaza-borolo[1,5-c]pyrimidinium-10-ide. Results of two single crystal X-ray structure analyses are presented.

  • 出版日期2014