Prev. Article Next Article Table of Contents

Communication

Osmium Tetroxide-Promoted Catalytic Oxidative Cleavage of Olefins: An Organometallic Ozonolysis

Supporting Info

Benjamin R. Travis, Radha S. Narayan, and Babak Borhan*

Department of Chemistry, Michigan State University, East Lansing, Michigan 48824

J. Am. Chem. Soc., 2002, 124 (15), pp 3824–3825

DOI: 10.1021/ja017295g

Publication Date (Web): March 22, 2002

To whom correspondence should be addressed. E-mail: borhan@cem.msu.edu.

Abstract

A mild, organometallic alternative to ozonolysis utilizing oxone and OsO₄ is presented. This is a direct oxidation of olefins via the carbon−carbon cleavage of an osmate ester by the action of oxone. Twenty-four different olefins were converted to their corresponding ketones or carboxylic acids in high yields (>80%). Free alcohols, acetate- and benzyl-protected alcohols, and 1,2-diols were stable under these conditions. This method should be applicable for traditional organic synthesis.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue April 17, 2002
Received October 12, 2001

Recommend & Share

Related Content

Improved Procedure for the Oxidative Cleavage of Olefins by OsO₄−NaIO₄Organic Letters
- Improved Procedure for the Oxidative Cleavage of Olefins by OsO₄−NaIO₄
  Wensheng Yu, Yan Mei, Ying Kang, Zhengmao Hua, and Zhendong Jin
  Organic Letters 2004 6 (19), pp 3217–3219
  Abstract: Oxidative cleavage of olefins by OsO₄−NaIO₄ sometimes suffers from low yields due to the formation of side products. It is found that the addition of 2,6-lutidine can suppress the side reactions and dramatically improve the yield of this classic reaction. ...
  Abstract | Full Text HTML | Hi-Res PDF
Ruthenium-Catalyzed Oxidative Cleavage of Olefins to AldehydesThe Journal of Organic Chemistry
- Ruthenium-Catalyzed Oxidative Cleavage of Olefins to Aldehydes
  Dan Yang and Chi Zhang
  The Journal of Organic Chemistry 2001 66 (14), pp 4814–4818
  Abstract: Three oxidation protocols have been developed to cleave olefins to carbonyl compounds with ruthenium trichloride as catalyst (3.5 mol %). These methods convert olefins that are not fully substituted to aldehydes rather than carboxylic acids. While aryl ...
  Abstract | Full Text HTML | Hi-Res PDF
Activated Iodosylbenzene Monomer as an Ozone Equivalent: Oxidative Cleavage of Carbon−Carbon Double Bonds in the Presence of WaterJournal of the American Chemical Society
- Activated Iodosylbenzene Monomer as an Ozone Equivalent: Oxidative Cleavage of Carbon−Carbon Double Bonds in the Presence of Water
  Kazunori Miyamoto, Norihiro Tada, and Masahito Ochiai
  Journal of the American Chemical Society 2007 129 (10), pp 2772–2773
  Abstract: Reported here for the first time are the developments of an efficient method for oxidative cleavage of carbon−carbon double bonds yielding carbonyl compounds by using aryl-λ³-iodanes, which involve a combination of iodosylbenzene and HBF₄ in the presence ...
  Abstract | Full Text HTML | Hi-Res PDF

Communication

Osmium Tetroxide-Promoted Catalytic Oxidative Cleavage of Olefins: An Organometallic Ozonolysis