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review
| Synthesis 1994; 1994: 639-666
DOI: 10.1055/s-1994-25538 |
© 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. |
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Tetrapropylammonium Perruthenate, Pr4N+RuO4-, TPAP: A Catalytic Oxidant for Organic Synthesis |
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| Steven V. Ley*, Joanne Norman, William P. Griffith, Stephen P. Marsden |
| *Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, England |
This article reviews the oxidations of a wide range of molecules with tetrapropylammonium perruthenate including examples of both double oxidations and selective oxidations. Mechanistic studies are discussed and general experimental procedures are reported. In addition several interesting developments in the chemistry of this reagent are outlined, that is, heteroatom oxidation, cleavage reactions and also its use in sequential reaction processes. In order to present a complete picture examples of failed reactions have been included. 1. Introduction 1.1. Oxoruthenates 1.2. Mechanistic Studies on [RuO4]- as an Oxidant 1.3. Experimental Considerations 1.4. Functional Group Compatibility and Selectivity 2. Primary Hydroxyl Group Oxidation 3. Secondary Hydroxyl Group Oxidation 4. Allylic and Benzylic Hydroxyl Group Oxidation 5. Lactol Oxidation 6. Heteroatom Oxidation 7. Cleavage Reactions 8. Tandem or Sequential Reaction Processes 9. Failed Reactions 10. Conclusions
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