Alkenes oxidation oxygen without catalyst

Aerobic oxidation of alkenes with a ruthenium catalyst has been explored by several groups. Groves et al. reported that Ru(TMP)(0)2 (34)-catalyzed aerobic epoxidation of alkenes proceeds under 1 atm of molecular oxygen without any reducing agent [111b]. 

However, most asymmetric 1,3-dipolar cycloaddition reactions of nitrile oxides with alkenes are carried out without Lewis acids as catalysts using either chiral alkenes or chiral auxiliary compounds (with achiral alkenes). Diverse chiral alkenes are in use, such as camphor-derived chiral N-acryloylhydrazide (195), C2-symmetric l,3-diacryloyl-2,2-dimethyl-4,5-diphenylimidazolidine, chiral 3-acryloyl-2,2-dimethyl-4-phenyloxazolidine (196, 197), sugar-based ethenyl ethers (198), acrylic esters (199, 200), C-bonded vinyl-substituted sugar (201), chirally modified vinylboronic ester derived from D-( + )-mannitol (202), (l/ )-menthyl vinyl ether (203), chiral derivatives of vinylacetic acid (204), ( )-l-ethoxy-3-fluoroalkyl-3-hydroxy-4-(4-methylphenylsulfinyl)but-1 -enes (205), enantiopure Y-oxygenated-a,P-unsaturated phenyl sulfones (206), chiral (a-oxyallyl)silanes (207), and (S )-but-3-ene-1,2-diol derivatives (208). As a chiral auxiliary, diisopropyl (i ,i )-tartrate (209, 210) has been very popular. 

A much more frequently used reaction is the cleavage of unsaturated compounds to aldehydes (equations 98 and 99). Alkenes and cycloalkenes that possess one or two hydrogens at the double bonds are oxidized by ozone to ozonides, which have to be reduced to prevent a subsequent oxidation to acids by the excess oxygen atom. Reductions are carried out, usually without isolation of the ozonides, by catalytic hydrogenation over palladium catalyst [80, 81,1106] or Raney nickel [55] or by treatment with... 

---