Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: an organometallic ozonolysis
BR Travis, RS Narayan, B Borhan
Index: Travis, Benjamin R.; Narayan, Radha S.; Borhan, Babak Journal of the American Chemical Society, 2002 , vol. 124, # 15 p. 3824 - 3825
Full Text: HTML
Citation Number: 185
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 ...
Related Articles:
Synthesis of phospholipids suitable for covalent binding to surfaces
[Kallury, R. Krishnamohanrao; Krull, Ulrich J.; Thompson, Michael Journal of Organic Chemistry, 1987 , vol. 52, # 24 p. 5478 - 5480]
Preparation of ω-hydroxynonanoic acid and its ester derivatives
[Kula, Jozef; Smigielski, Krzysztof; Quang, Thuat B.; Grzelak, Iwona; Sikora, Magdalena JAOCS, Journal of the American Oil Chemists' Society, 1999 , vol. 76, # 7 p. 811 - 817]
[Wiberg, Kenneth B.; Waldron, Roy F. Journal of the American Chemical Society, 1991 , vol. 113, # 20 p. 7697 - 7705]
Omega-hydroxy aliphatic acids. Synthesis of sabinic acid
[Lycan; Adams Journal of the American Chemical Society, 1929 , vol. 51, p. 627]
[Chapuis, Christian; Robvieux, Fabrice; Cantatore, Carole; Saint-Leger, Christine; Maggi, Laurent Helvetica Chimica Acta, 2012 , vol. 95, # 3 p. 428 - 447]