Spontaneous and Selective Macrocyclization in Nitroaldol Reaction Systems
Yunchuan Qi1, Mubarak Ayinla1, Stephen Clifford1
1Department of Chemistry, University of Massachusetts Lowell, One University Ave., Lowell, Massachusetts 01854, United States.
Abstract:
Through a dynamic polymerization and self-sorting process, a range of lowellane macrocycles have been efficiently generated in nitroaldol systems composed of aromatic dialdehydes and aliphatic or aromatic dinitroalkanes. All identified macrocycles show a composition of two repeating units, resulting in tetra-β-nitroalcohols of different structures. The effects of the building block structure on the macrocyclization process have been demonstrated, and the influence from the solvent has been explored. In general, the formation of the lowellanes was amplified in response to phase-change effects, although solution-phase structures were, in some cases, favored.
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