If anyone has access to the full version of Organic Reactions online, feel free to post the missing tables not available in the DjVu file below.
Dioxirane Epoxidation of Alkenes
Waldemar Adam, Chantu R. Saha-Möller, Cong-Gui Zhao, John Wiley & Sons, Inc. (2002)
Org. React. 61, Chapter 2, pp. 219-264 + 508-516 (https://www.thevespiary.org/rhodium/Rhodium/djvu/or61.dioxirane.epoxidation.adam.djvu)
(https://www.thevespiary.org/rhodium/Rhodium/djvu/or61.dioxirane.epoxidation.adam.djvu) (sans tables, provided by lugh)
DOI:10.1002/0471264180.or061.02 (http://dx.doi.org/10.1002/0471264180.or061.02)
Abstract
1. Introduction
2. Mechanism
3. Scope and Limitations
4. Comparison with Other Methods
5. Experimental Conditions
6. Experimental Procedures
7. Tabular Survey
8. Acknowledgments
References
Keywords: dioxirane; epoxidation; alkenes; unfunctionalized alkenes; electron-rich; electron poor; electron donor; electron acceptor; chemoselectivity; regioselectivity; diastereoselectivity; entioselectivity; scope; limitations; oxidation; solvents; temperature; neutral conditions; basic conditions; homogeneous media; comparison of methods; experimental conditions; experimental procedures; tabular survey
Abstract
An ideal oxidant should be highly reactive, selective, and environmentally benign. It should transform a broad range of substrates with diverse functional groups, preferably under catalytic conditions, and be readily generated from commercially available and economical starting materials. Of course, such an ideal oxidant has not yet been invented; however, the dioxiranes, which have risen to prominence during the past few decades, appear to fulfill these requirements in many respects. These three membered ring cyclic peroxides are very efficient in oxygen transfer, yet very mild toward the substrate and product. They exhibit chemo-, regio-, diastereo-, and enantioselectivities, act catalytically, and can be readily prepared from a suitable ketone (for example, acetone) and potassium monoperoxysulfate (2KHSO5·K2SO4·KHSO4, Caroate®, Oxone®, or Curox®), which are low-cost commercial bulk chemicals. Throughout the text KHSO5 is used to specify this oxygen source, rather than refer to one of the commercial trade names.