Alkenes to aldehydes/ketones

Abstract This chapter covers one of the most important areas of Ru-catalysed oxidative chemistry. First, alkene oxidations are covered in which the double bond is not cleaved (3.1) epoxidation, cis-dihydroxylation, ketohydroxylation and miscellaneous non-cleavage reactions follow. The second section (3.2) concerns reactions in which C=C bond cleavage does occur (oxidation of alkenes to aldehydes, ketones or carboxylic acids), followed by a short survey of other alkene cleavage oxidations. Section 3.3 covers arene oxidations, and finally, in section 3.4, the corresponding topics for aUcyne oxidations are considered, most being cleavage reactions. 

Oxidative cleavage of alkenes to aldehydes, ketones or carboxylic acids is an important transformation usually carried out by ozonolysis or oxidation with stoichiometric oxidants, i.e. OSO4, MnO 1 etc.199. The serious drawbacks of most of these reagents,... 

As stated in the previous sections, the chief drawbacks in reactions using osmium tetroxide are its volatility, toxicity, and high cost. The less expensive and hazardous isoelectronic ruthenium tetroxide has long been appreciated for its powerful oxidation chemistry, especially oxidative cleavage of alkenes to aldehydes, ketones, and carboxylic acids [57]. Sharpless and Akashi showed for the first time that RUO4 can... 

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