Observations and comments on the mechanism of epoxidation of alkenes by manganese(III) porphyrins with hypochlorite. | Zendy

R. W. Lee | Zendy; Paul C. Nakagaki | Zendy; P. N. Balasubramanian | Zendy; Thomas C. Bruice | Zendy

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Observations and comments on the mechanism of epoxidation of alkenes by manganese(III) porphyrins with hypochlorite.

Author(s) -

R. W. Lee,

Paul C. Nakagaki,

P. N. Balasubramanian,

Thomas C. Bruice

Publication year - 1988

Publication title -

proceedings of the national academy of sciences

Language(s) - English

Resource type - Journals

eISSN - 1091-6490

pISSN - 0027-8424

DOI - 10.1073/pnas.85.3.641

Subject(s) - manganese , porphyrin , chemistry , hypochlorite , photochemistry , inorganic chemistry , olefin fiber , hypervalent molecule , catalysis , reagent , reaction rate constant , organic chemistry , kinetics , physics , quantum mechanics

The kinetics of olefin epoxidation in a methylene chloride/water biphase containing a phase-transfer agent with hypochlorite as oxygen transfer reagent and manganese(III) tetraphenylporphyrin catalysts has been reinvestigated. The results do not support the accumulation of an intermediate composed of an alkene and a hypervalent metaloxo porphyrin. Second-order rate constants for oxygen transfer from hypochlorite to the manganese porphyrin, comproprotionation of the hypervalent manganese-oxo porphyrin with manganese(III) porphyrin, and olefin epoxidation by the hypervalent manganese-oxo porphyrin were obtained from experiments in a wet organic monophase.

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