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

Xiaotai Wang; L. Keith Woo

doi:10.1021/jo971893p

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

Xiaotai Wang, L. Keith Woo^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

25 Citations (Scopus)

Abstract

Treatment of the well-defined complexes (TTP)Ti(η²-EtC≡CEt) or transs-(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)Ti=O, 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.

Original language	English
Pages (from-to)	356-360
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	63
Issue number	2
DOIs	https://doi.org/10.1021/jo971893p
Publication status	Published - 23 Jan 1998
Externally published	Yes

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Wang, X., & Keith Woo, L. (1998). Titanium(II) Porphyrin Complexes: Versatile One- And Two-Electron Reducing Agents. Reduction of Organic Chlorides, Epoxides, and Sulfoxides. Journal of Organic Chemistry, 63(2), 356-360. https://doi.org/10.1021/jo971893p

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

abstract = "Treatment of the well-defined complexes (TTP)Ti(η2-EtC≡CEt) or transs-(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)Ti=O, 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.",

author = "Xiaotai Wang and {Keith Woo}, L.",

year = "1998",

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N2 - Treatment of the well-defined complexes (TTP)Ti(η2-EtC≡CEt) or transs-(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)Ti=O, 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.

AB - Treatment of the well-defined complexes (TTP)Ti(η2-EtC≡CEt) or transs-(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)Ti=O, 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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Titanium(II) Porphyrin Complexes: Versatile One- And Two-Electron Reducing Agents. Reduction of Organic Chlorides, Epoxides, and Sulfoxides

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