16. Silyl Migrations

  1. Zvi Rappoport2 and
  2. Yitzhak Apeloig3
  1. Mitsuo Kira and
  2. Takeaki Iwamoto

Published Online: 18 JUL 2003

DOI: 10.1002/0470857269.ch16

The Chemistry of Organic Silicon Compounds, Volume 3

The Chemistry of Organic Silicon Compounds, Volume 3

How to Cite

Kira, M. and Iwamoto, T. (2001) Silyl Migrations, in The Chemistry of Organic Silicon Compounds, Volume 3 (eds Z. Rappoport and Y. Apeloig), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470857269.ch16

Editor Information

  1. 2

    The Hebrew University, Jerusalem, Israel

  2. 3

    Israel Institute of Technology, Haifa, Israel

Author Information

  1. Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980–8578, Japan. Fax: 81-22-217-6589

Publication History

  1. Published Online: 18 JUL 2003
  2. Published Print: 10 DEC 2001

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Zvi Rappoport

Series Editor Information

  1. The Hebrew University, Jerusalem, Israel

ISBN Information

Print ISBN: 9780471623847

Online ISBN: 9780470857267

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Summary

This chapter contains sections titled:

  • Introduction

  • 1,2-silyl Migrations

    • Mechanistic Aspects

      • Dyotropic and Related Rearrangements

      • Cationic 1,2-silyl Migrations and Related 1,2-migrations

      • Anionic 1,2-silyl Migrations

      • Radical 1,2-silyl Migrations

      • Miscellaneous

    • 1,2-silyl Migrations in Unsaturated Silicon Compounds

      • Silylmethylsilylene–silylsilaethene Rearrangements

      • Disilanylcarbene–silylsilaethene Rearrangements

      • Silylsilanone–siloxysilylene Rearrangements

      • Disilanylsilylene–silyldisilene Rearrangements

      • Disilanyldisilene–2-silylcyclotrisilane Rearrangements

    • Synthetic Applications

      • Cationic 1,2-silyl Migrations from C to C

        • [3+2] Annulations

        • [2+1] Annulations

        • Intramolecular Cyclizations and Ring Openings

        • Miscellaneous

      • Anionic 1,2-silyl Migrations from C to O

        • Preparation of Silyl Enol Ethers

        • Cyclizations Involving the Brook Rearrangement

        • Miscellaneous

      • Anionic 1,2-silyl Migrations from O to C

      • Anionic 1,2-silyl Migrations between C and N

      • Radical 1,2-silyl Migrations

  • 1,3-silyl Migrations

    • Mechanistic Aspects

      • Migrations Across Allylic Frameworks

      • 1,3-silyl Migrations in Allylsilanes

      • 1,3-silyl Migrations in β-ketosilanes

      • Comparison of the Retention Transition States for 1,3-silyl Migrations in Allylsilane and Formylmethylsilane

      • Anionic 1,3-silyl Migrations Across σ Frameworks

    • 1,3-silyl Migrations in Unsaturated Silicon Compounds

    • Synthetic Applications

  • 1,n-silyl Migrations (n ≥ 4)

    • 1,4-silyl Migrations

      • 1,4-silyl Migration from C to C

      • Anionic 1,4-silyl Migrations from C to O

      • Anionic 1,4-silyl Migrations from O to C

      • Anionic 1,4-silyl Migrations from O to O

      • Anionic 1,4-silyl Migrations Incorporating N

    • 1,5-silyl Migrations

      • 1,5-silyl Migrations between C and O

      • 1,5-silyl Migrations from O to N

      • 1,5-silyl Migrations from O to O

      • 1,5-silyl Migrations from Si to C

    • 1,6-silyl Migrations

  • References