CHED 880 |
Synthesis of β-linked dipyrroalkanes
| G. Richard Geier III, Waldemar Auguscinski, and Jennifer B. Callinan. Department of Chemistry, Colgate University, 13 Oak Drive, Hamilton, NY 13346 |
A synthetic route leading to β-linked dipyrroalkanes was developed. The three step synthesis began with the preparation of 3-bromo-TIPS-pyrrole via bromination of TIPS-pyrrole with NBS. Treatment of the 3-bromo-TIPS-pyrrole with t-butyllithium, followed by the addition of a diiodoalkane provided a TIPS-protected β-linked dipyrroalkane. Removal of the TIPS-groups with TBAF afforded the target compound. β-Linked dipyrrobutane and dipyrropentane were prepared via this synthetic route. These β-linked dipyrroalkanes may be used as building blocks in the stepwise synthesis of expanded porphyrinic macrocycles with unusual core structures. |
| |
|
|