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

Iowa State University
University of Colorado Denver

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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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",

month = jan,

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doi = "10.1021/jo971893p",

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journal = "Journal of Organic Chemistry",

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T1 - Titanium(II) Porphyrin Complexes

T2 - Versatile One- And Two-Electron Reducing Agents. Reduction of Organic Chlorides, Epoxides, and Sulfoxides

AU - Wang, Xiaotai

AU - Keith Woo, L.

PY - 1998/1/23

Y1 - 1998/1/23

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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U2 - 10.1021/jo971893p

DO - 10.1021/jo971893p

M3 - Article

AN - SCOPUS:0006597890

SN - 0022-3263

VL - 63

SP - 356

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 2

ER -

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

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