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Synlett 1993; 1993(2): 97-104
DOI: 10.1055/s-1993-22362
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Balancing Leaving Group Ability and the ß-Effect: Exploring the Synthetic Utility of Chlorosilyl Groups

Michael A. Brook* , Courtney Henry, Ralf Jueschke, Pankaj Modi
  • *Department of Chemistry, McMaster University, 1280 Main St. W., Hamilton, Ontario, Canada L8S 4M1
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Publication Date:
19 March 2002 (online)

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Chlorosilanes have generally been ignored in the area of organic synthesis. It is demonstrated that these materials have a diminished but significant ß-effect when compared to trialkylsilyl species and, as importantly, a lower leaving group ability. The utility of chlorosilyl groups in addition reactions to styrylsilanes is described. 1. Introduction 2. Silicon as a Leaving Group: Mechanistic Implications 3. Determining the Relative ß-Effect 4. Addition Reactions to Styrylsilanes 4.1. Acylation 4.2. Addition of Alkyl Cations 4.3. Protonation 5. Other Intramolecular Additions 6. Controlled Cyclization 7. Conclusion