Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 8, Pages 5449-5463Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00197
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Funding
- National Science Foundation [CHE 1465113]
- National Institutes of Health [GM132531-01]
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Outlined here are studies exploring the scope of the sequential photoelectrocyclization, [1,5]-hydride shift of conjugated bis-aryl cycloalkenone substrates. We have found not only that the cyclization precursors can be synthesized in a modular fashion but also that the cyclization is efficient and amenable to the presence of a range of cycloalkenones and aromatic systems. Among the interesting discoveries from this work is that the electrocyclization intermediate can be competitively captured with protons and that the nature of the excited state (singlet vs triplet) is dependent on aromatic substitution.
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