Chapter 6. Insertion Reactions of the Stable Silylene Si[(NCH2tBu)2C6H4-1,2]

  1. Prof. Dr. Norbert Auner2 and
  2. Prof. Dr. Johann Weis3
  1. Floria Antolini,
  2. Xiaoping Cai,
  3. Barbara Gehrhus,
  4. Peter B. Hitchcock,
  5. Michael F. Lappert,
  6. Massimo Parrucci and
  7. J. Chris Slootweg

Published Online: 5 MAY 2008

DOI: 10.1002/9783527619924.ch6

Organosilicon Chemistry V: From Molecules to Materials

Organosilicon Chemistry V: From Molecules to Materials

How to Cite

Antolini, F., Cai, X., Gehrhus, B., Hitchcock, P. B., Lappert, M. F., Parrucci, M. and Slootweg, J. C. (2003) Insertion Reactions of the Stable Silylene Si[(NCH2tBu)2C6H4-1,2], in Organosilicon Chemistry V: From Molecules to Materials (eds N. Auner and J. Weis), Wiley-VCH Verlag GmbH, Weinheim, Germany. doi: 10.1002/9783527619924.ch6

Editor Information

  1. 2

    Department of Inorganic Chemistry, University of Frankfurt, Marie-Curie-Straße 11, 60439 Frankfurt am Main, Germany

  2. 3

    Consortium of Electrochemical Industry GmbH, Zielstattstraße 20, 81379 Munich, Germany

Author Information

  1. The Chemistry Laboratory, University of Sussex, Brighton, BN1 9QJ, UK Tel.: +44 01273 606755 — Fax: +44 01273 677196

Publication History

  1. Published Online: 5 MAY 2008
  2. Published Print: 26 SEP 2003

ISBN Information

Print ISBN: 9783527306701

Online ISBN: 9783527619924

SEARCH

Keywords:

  • insertion;
  • silylene;
  • amino-functionalised silyl anions

Summary

The silylene Si[(NCH2tBu)2C6H4-1,2] 1 inserts readily into the Li–C, Li–Si or M–N (M = Li, Na or K) bond of the lithium alkyl LiR [R = Me, tBu or CH(SiMe3)2], the lithium sisyl Li[Si(SiMe3)3], or the alkali metal amide MNR'R″ (M = Li, Na or K, R' = R″ = SiMe3; M = Li, R' = SiMe3 and R″ = 2,6–Me2C6H3, or R' = R″ = Me or iPr) to yield the corresponding amino-functionalized lithium silyl for LiR, Li[Si(SiMe3)3] and LiNR'R″ (R' = R″ = Me or iPr), but alkali amide for MNR'R″ (R' = R″ = SiMe3). Insertion of 1 into the Li-N bond of the lithium enamide Li[N(SiMe2OMe)(AdC[DOUBLE BOND]CHSiMe3)] (Ad = 1-adamantyl) affords a new azatrisilacyclobutane. The mechanism of the reactions will be discussed.