Download PDF
Synlett 1995; 1995(7): 745-747
DOI: 10.1055/s-1995-5076
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.

A One-pot Conversion of Propargylic Bromides to Allenyl-, Propargyl- and 1-Propynyllithiums

Takahiro Kanda1 , Yoshio Ando1 , Shinzi Kato1 , Nobuaki Kambe2 , Noboru Sonoda2
  • 1Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-11, Japan
  • 2Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita Osaka 565, Japan
Further Information

Publication History

Publication Date:
31 December 2000 (online)

 PDF Download  Permissions and Reprints All articles of this category

Reaction of BuTeLi with propargylic bromides yields corresponding allenic and/or propargylic tellurides. The subsequent Li-Te exchange of the tellurides at low temperatures affords allenyl- and/or propargyllithiums. Thus formed propa-1,2-dienyllithium rearranges to 1-propynyllithium in refluxing THF. These organolithiums were trapped with carbonyl compounds to give homopropargylic and propargylic alcohols.

Li-Te exchange - propargylic bromides - propargyllithium - allenyllithium - 1-propynyllithium