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Sulfonium ylides derived from 2-hydroxy-benzoquinones: crystal and molecular structure and their one-step conversion into Mannich bases by amine N-oxides |
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| Authors: | Thomas Rosenau Kurt Mereiter Peter Schmid |
| Institution: | a Department of Chemistry, University of Natural Resources and Applied Life Sciences Vienna, Muthgasse 18, A-1190 Vienna, Austria b Department of Chemistry, Vienna University of Technology, Getreidemarkt 9, A-1060 Vienna, Austria c Federal Institute of Materials Research and Testing, Project Group I.3903, Richard-Willstaetter-Str. 11, D-12489 Berlin, Germany |
| Abstract: | Reaction of 2-hydroxy-para-benzoquinones with DMSO/Ac2O produced dimethylsulfonium ylides, of which crystal structures as well as solid and liquid state NMR spectra were recorded. The ylides react with tertiary methylamine N-oxides in a one-pot, multi-step process to 3-methylamino-substituted benzoquinones. The mechanism starts with a deoxygenative deprotonation of the amine N-oxides, followed by a formal electrophilic displacement of DMSO by the resulting carbonium-iminium ion. |
| Keywords: | Sulfonium ylides Amine N-oxides Crystal structure Benzoquinones |
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