Tetrahedron

Sulfonium ylides derived from 2-hydroxy-benzoquinones: crystal and molecular structure and their one-step conversion into Mannich bases by amine N-oxides

T Rosenau, K Mereiter, C Jäger, P Schmid, P Kosma

文献索引：Rosenau, Thomas; Mereiter, Kurt; Jaeger, Christian; Schmid, Peter; Kosma, Paul Tetrahedron, 2004 , vol. 60, # 27 p. 5719 - 5723

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被引用次数: 5

摘要

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 ...