Molecular Rearrangements in Lithium Aluminum Hydride Reduction

Shi-Chow CHEN

doi:10.1055/s-1974-23404

Synthesis 1974; 1974(10): 691-703
DOI: 10.1055/s-1974-23404

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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

Abstract

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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.

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