1,1,3,3-Tetrakis(alkylthio)-1,3-dilithio-2-silapropanes: Useful reagents for the synthesis of polysilacycloalkanes via dianionic ring formation

Masaki Shimizu, Masayuki Iwakubo, Yasushi Nishihara, Katsunari Oda, Tamejiro Hiyama

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Treatment of 1,1,3,3-tetrakis(alkylthio)-2-silapropanes with t-BuLi in THF at -40°C generated 1,1,3,3-tetrakis(alkylthio)-1,3-dilithio-2-silapropanes which reacted with various bifunctional chlorosilanes to give the corresponding 4- to 7-membered polysilacycloalkanes in moderate to good yields. Furthermore, double alkylation of the dilithiated silanes with bis(halomethyl)diorganosilanes or dihaloalkanes was found to proceed smoothly giving rise to 1,4-disilacyclohexanes or silacycloalkanes in good yields, respectively, in THF and an aprotic polar co-solvent such as hexamethylphosphoric triamide (HMPA) or 1,1,3,3-tetramethylurea (TMU). The sulfenyl groups in the cyclized products were smoothly removed by radical reduction with tributyltin hydride.

Original languageEnglish
Pages (from-to)29-48
Number of pages20
JournalArkivoc
Volume2007
Issue number10
DOIs
Publication statusPublished - 2007

Keywords

  • Dianion
  • Lithium
  • Polysilacycloalkane
  • Silicon

ASJC Scopus subject areas

  • Organic Chemistry

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