Download PDF
Synthesis 2000; 2000(3): 452-456
DOI: 10.1055/s-2000-6336
paper
© 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.

Generation of Acetylides by Treatment of Fluoroethylenes with LDA: Preparation of Propargyl Alcohols

Kentaro Kataoka* , Sadao Tsuboi
  • *Department of Applied Chemistry, Faculty of Engineering, Okayama University, Tsushima, Okayama 700-8530, Japan; Fax +81 (86) 2 51 88 98; E-mail: stsuboi6@cc.okayama-u.ac.jp
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

The fluoroethylenes 3 produced the corresponding acetylides via dehydrofluorination and deprotonation by treatment with 2 equivalents of LDA in THF at 0 °C. These acetylides reacted with aldehydes and ketones to afford propargyl alcohols in good yields.

Wittig reaction - fluoroethylenes - dehydrofluorination - acetylides - propargyl alcohols - fluorine - eliminations