期刊
SYNTHESIS-STUTTGART
卷 53, 期 24, 页码 4567-4587出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1577-5864
关键词
Stevens rearrangement; diazoalkanes; carbenes; carbene transfer reaction; ylides; [1,2]-sigmatropic rearrangement
资金
- Deutsche Forschungsgemeinschaft (German Research Foundation)
- Fonds der Chemischen Industrie e.V.
This review article summarizes the progress made on [1,2]-sigmatropic rearrangements using carbenes in the ylide formation step, highlighting the application of diazoalkanes as carbene precursors and the formation and application of various ylide species.
This review article summarizes progress made on [1,2]-sigmatropic rearrangements using carbenes in the ylide formation step. While other rearrangements, such as the [2,3]-sigmatropic, Doyle-Kirmse, or Sommelet-Hauser rearrangements, have been studied in detail over the past decades, investigations on [1,2]-sigmatropic rearrangements are still limited. Based on the application of diazoalkanes as carbene precursors, research on diazoalkanes in ylide formation reactions started flourishing in the 1990s. This Short Review covers milestones from the advent of [1,2]-sigmatropic rearrangements using carbenes to generate ammonium, oxonium and other ylide species, and should serve as an overview to further promote research in this area. 1 Introduction 2 Ammonium Ylides 3 Oxonium Ylides 4 Sulfonium and Selenium Ylides 5 Halonium Ylides 6 Conclusion and Outlook
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