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- Title
Copper-Mediated Nitrosation: 2-Nitrosophenolato Complexes and Their Use in the Synthesis of Heterocycles.
- Authors
Nicholls, Alexander J.; Batsanov, Andrei S.; Baxendale, Ian R.
- Abstract
A simple protocol yielding ortho-substituted nitrosophenols from phenols is demonstrated, in the form of copper(II) bis(nitrosophenolato) complexes. The developed methodology was applied to a range of substrates, confirming the role of the copper in both the formation and protection of the challenging 1, 2-substitution pattern. Using polymer supported thiourea, the Cu could be stripped from the complexes and thus enabled the isolation or identification of the uncoordinated ligands and their decomposition products, in yields generally low in line with the intrinsic high reactivity of 2-nitrosophenols. The product complexes are useful intermediates as demonstrated in revisiting a formal [4 + 2] cycloaddition with dimethylacetylene dicarboxylate to synthesise bicyclic products in variable yields, revealing the product has a novel structure different from those previously reported in the literature.
- Subjects
NITROSATION; HETEROCYCLIC compounds; POLYMERS; PHENOLS; RING formation (Chemistry)
- Publication
Molecules, 2019, Vol 24, Issue 22, p4154
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules24224154