Papers

2007

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

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

First page
29
Last page
48
Language
English
Publishing type
Research paper (scientific journal)
Publisher
ARKAT USA INC

Treatment of 1,1,3,3-tetrakis(alkylthio)-2-silapropanes with t-BuLi in THF at -40 degrees 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.

Link information
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000251573000005&DestApp=WOS_CPL
ID information
  • ISSN : 1551-7004
  • Web of Science ID : WOS:000251573000005

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