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Review | Regular issue | Vol 6, No. 5, 1977, pp.583-675
Published online, 1st January, 1970
DOI: 10.3987/R-1977-05-0583
Rearrangementws of t-Amine Oxides

Shigeru Oae* and Kenji Ogino

*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan


Heteroaromatic N-oxides and related tertiary amine oxides react with acylating agents and undergo various reactions depending upon the nature of the amine oxides, acylating agents,etc. These reactions are broadly divided into the following five basic types of reactions: 1) deoxygenative reduction, 2) rearrangement to ring carbon, 3) rearrangement to side chain carbon, 4) other heteroaromatic rearrangements, 5) rearrangements of open-chain N-oxides.
Each of these five representative reactions are illustrated by numerous examples, including many of our mechanistic investigations, hoping eventually to serve as nice guides to new synthetic inventions and innovations. The contents of this review are the following:
1. Introduction
2. Deoxygenative Reduction of N-oxides
3. Reactions with acylating agents : Rearrangements to heteroaromatic ring
4. Reactions with acylating agents : Rearrangements to alkyl side-chain
5. Other related rearrangements of heteroaromatic N-oxides
6. Reactions of non-heteroaromatic N-oxides with acylating agents : Aliphatic t-amine
oxides, nitrones and azoxybenzenes
7. Acknowledgement