Download PDF
Synlett 1998; 1998(10): 1096-1098
DOI: 10.1055/s-1998-1898
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Regioselective Reaction of Dilithiated 1-Alkynylsilanol with Electrophiles

S. Uehira* , K. Takaku, H. Shinokubo, K. Oshima
  • *Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan; Fax + 81-75-761-8846; E-mail: oshima@fm1.kuic.kyoto-u.ac.jp
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Treatment of 1-propynylsilanol 1a with two equivalents of tert-butyllithium in THF in the presence of HMPA at -78 °C afforded silylpropynyllithium 2a bearing an anionic oxygen on the silicon atom. The reaction of 2a with various electrophiles gave acetylenic adducts in good yields. Higher regioselectivities were achieved in the reaction of silyl-substituted propynyllithium derived from potassium silanolate.

silanol - alkynylsilane - propargyllithium - allene - alkyne

      >