Titanium(II) Porphyrin Complexes: Versatile One- and Two-Electron Reducing Agents. Reduction of Organic Chlorides, Epoxides, and Sulfoxides | Zendy

Xiaotai Wang | Zendy; L. Keith Woo | Zendy

Open Access

Titanium(II) Porphyrin Complexes: Versatile One- and Two-Electron Reducing Agents. Reduction of Organic Chlorides, Epoxides, and Sulfoxides

Author(s) -

Xiaotai Wang,

L. Keith Woo

Publication year - 1998

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo971893p

Subject(s) - chemistry , redox , alkene , electron transfer , deoxygenation , porphyrin , sulfide , yield (engineering) , photochemistry , sulfoxide , medicinal chemistry , vicinal , catalysis , organic chemistry , materials science , metallurgy

Treatment of the well-defined complexes (TTP)Ti(η2-EtC⋮CEt) or trans-(TTP)Ti(THF)2 with vicinal dichloroalkanes or dichloroalkenes results in the production of alkenes or alkynes and 2 equiv of (TTP)TiCl. This net two-electron redox reaction arises from two formal one-electron reduction processes mediated by chlorine atom transfer. Oxygen atom transfer occurs when the Ti(II) porphyrins are treated with several different sulfoxides or epoxides, resulting in two-electron redox products, (TTP)TiO, the sulfide or alkene, and EtC⋮CEt or THF. The electronic properties of the substituents on the sulfoxides or epoxides correlate with the yield and rate of the deoxygenation reactions.

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