Alkene Cleavage to Aldehydes or Ketones

These are relatively rare reactions for RuO - as with primary alcohols, further oxidation to carboxylic acids normally occurs. Examples are given in Table 3.3. Generally, under neutral conditions, aldehydes are formed but under acidic or alkaline conditions carboxylic acids are the main oxidation products. 

1 Specific Examples of Alkene Cleavage to Aldehydes and Ketones 

As part of a preparation of marine odourants, oxidation by RuCyaq. Na(lO )/ CCl of the =CH3 moiety in the marine floral-aldehyde 1-methyl-7-methylene-2,3,7,8-tetrahydro-l//,6//-5,9-dioxacyclohepta[/]indene gave l-methyl-2,3-di-hydro-l//-5,9-dioxa-cyclohepta[/]-inden-7-one (Fig. 3.16) [200]. 

A mono-fluorinated alkene has recently been oxidised to the corresponding ketone by RuCyaq. Na(IO )/CgHj3-CH3CN. Hydrolysis of the CF unit to C=0 did not occur in contrast neutral aq. I nO gave no ketone but there was extensive hydrolysis, c/ 1.11 

Reactant Product (major product listed first) Method [Ref.] 

---