PDF herunterladen
Synthesis 1974; 1974(10): 691-703
DOI: 10.1055/s-1974-23404
review
© 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.

Molecular Rearrangements in Lithium Aluminum Hydride Reduction

Shi-Chow CHEN*
  • *Chemistry Department, National Chung-Hsing University, Taichung, Taiwan and Department of Chemistry & Chemical Engineering, University of Saskatchewan, Saskatoon, Saskatchewan, Canada
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
27. März 2002 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

Lithium aluminum hydride shows selective properties as a reducing agent and a Lewis acid. Several types of reductive rearrangements are surveyed and correlated on the basis of common unifying mechanistic principles. Rearrangement reactions which follow a predictable pathway offer real synthetic interest. 1. Structures and Properties of the Transition States and Intermediates of Organometallic Complexes. 2. Allylic Rearrangements. 2.1. Homoallylic Rearrangements and Cyclopropane Formations. 2.2. Enol Ethers. 2.3. Allylic Acetals and Oxiranes. 3. Rearrangements Involving Nitrogen Functional Groups. 3.1. Aziridine Formations. 3.2. Ring Enlargements and Ring Contractions. 4. Skeletal Rearrangements. 4.1. Base-Catalyzed Rearrangements. 4.2. Wagner-Meerwein and Pinacolic Rearrangements. 5. Addendum.