Oxidation olefin-sulphide systems

Metal phthalocyanines have been found to catalyze the oxidation of sulphides to sulphones at room temperature by molecular oxygen (1 atm) in the presence of isobutyraldehyde as sacrificial aldehyde. Among the metal phthalocyanines studied those of Fe(II), Mn(II) and Co(II)tetrasulphonato- showed excellent activity, followed by VO, while those of Ni(II) and Cu(II) were found to be least active for sulfide oxidation. Mn(II)phthalocyanine catalyzed epoxidation of olefins with molecular oxygen -isobutyraldehyde systems is also reported. 

In continuation to our studies with molecular oxygen as the primary oxidant[8], we now report metal phthalocynanine catalyzed oxidation of sulphides to sulphones and olefins to epoxides by dioxygen-isobutyraldehyde system under ambient conditions (Scheme-1). 

Solvolysis of the bicyclic mesylate (69) gave a mixture of rearranged olefins which were hydrogenated to give the hydroazulene (70). Oxyallyl cations react with phosphole sulphides and phosphole oxides to give the expected 8-phosphabicyclo [3,2,l]octanoic systems together with other products. ... 

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