Hydroxylation and expoxidation reactions catalyzed by synthetic metalloporphyrinates. Models related to the active oxygen species of cytochrome P-450

John T. Groves; William J. Kruper; Thomas E. Nemo; Richard S. Myers

doi:10.1016/0304-5102(80)85016-4

Hydroxylation and expoxidation reactions catalyzed by synthetic metalloporphyrinates. Models related to the active oxygen species of cytochrome P-450

John T. Groves, William J. Kruper, Thomas E. Nemo, Richard S. Myers

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Abstract

Iodosylbenzene has been found to react with catalytic amounts of synthetic metalloporphyrinates to give epoxides and alcohols from olefins and alkanes. Tetraphenylporphinatoiron(III) chloride (TPPFeCl) catalyzed the epoxidation of cis-stilbene to cis-stilbene oxide whereas the trans isomer was unreactive. Dioctyl protoporphyrin IX reacted with iodosylbenzene to give significant oxidation of the side chain alkyl groups. The distribution of products is interpreted to be the result of an intramolecular oxygen transfer reaction. Treatment of tetra-ortho-tolylporphinatoiron(III) chloride (TTPFeCl) with iodosylbenzene afforded a reactive intermediate which degraded the porphyrin in the absence of a oxidizable substrate. Similar oxidation of tetraphenylporphinatochromium(III) chloride with iodosylbenzene gave a stable intermediate which has been characterized as an oxochromium(V) complex.

Original language	English (US)
Pages (from-to)	169-177
Number of pages	9
Journal	Journal of Molecular Catalysis
Volume	7
Issue number	2
DOIs	https://doi.org/10.1016/0304-5102(80)85016-4
State	Published - Feb 1980
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Engineering

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10.1016/0304-5102(80)85016-4

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title = "Hydroxylation and expoxidation reactions catalyzed by synthetic metalloporphyrinates. Models related to the active oxygen species of cytochrome P-450",

abstract = "Iodosylbenzene has been found to react with catalytic amounts of synthetic metalloporphyrinates to give epoxides and alcohols from olefins and alkanes. Tetraphenylporphinatoiron(III) chloride (TPPFeCl) catalyzed the epoxidation of cis-stilbene to cis-stilbene oxide whereas the trans isomer was unreactive. Dioctyl protoporphyrin IX reacted with iodosylbenzene to give significant oxidation of the side chain alkyl groups. The distribution of products is interpreted to be the result of an intramolecular oxygen transfer reaction. Treatment of tetra-ortho-tolylporphinatoiron(III) chloride (TTPFeCl) with iodosylbenzene afforded a reactive intermediate which degraded the porphyrin in the absence of a oxidizable substrate. Similar oxidation of tetraphenylporphinatochromium(III) chloride with iodosylbenzene gave a stable intermediate which has been characterized as an oxochromium(V) complex.",

author = "Groves, {John T.} and Kruper, {William J.} and Nemo, {Thomas E.} and Myers, {Richard S.}",

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doi = "10.1016/0304-5102(80)85016-4",

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T1 - Hydroxylation and expoxidation reactions catalyzed by synthetic metalloporphyrinates. Models related to the active oxygen species of cytochrome P-450

AU - Groves, John T.

AU - Kruper, William J.

AU - Nemo, Thomas E.

AU - Myers, Richard S.

PY - 1980/2

Y1 - 1980/2

N2 - Iodosylbenzene has been found to react with catalytic amounts of synthetic metalloporphyrinates to give epoxides and alcohols from olefins and alkanes. Tetraphenylporphinatoiron(III) chloride (TPPFeCl) catalyzed the epoxidation of cis-stilbene to cis-stilbene oxide whereas the trans isomer was unreactive. Dioctyl protoporphyrin IX reacted with iodosylbenzene to give significant oxidation of the side chain alkyl groups. The distribution of products is interpreted to be the result of an intramolecular oxygen transfer reaction. Treatment of tetra-ortho-tolylporphinatoiron(III) chloride (TTPFeCl) with iodosylbenzene afforded a reactive intermediate which degraded the porphyrin in the absence of a oxidizable substrate. Similar oxidation of tetraphenylporphinatochromium(III) chloride with iodosylbenzene gave a stable intermediate which has been characterized as an oxochromium(V) complex.

AB - Iodosylbenzene has been found to react with catalytic amounts of synthetic metalloporphyrinates to give epoxides and alcohols from olefins and alkanes. Tetraphenylporphinatoiron(III) chloride (TPPFeCl) catalyzed the epoxidation of cis-stilbene to cis-stilbene oxide whereas the trans isomer was unreactive. Dioctyl protoporphyrin IX reacted with iodosylbenzene to give significant oxidation of the side chain alkyl groups. The distribution of products is interpreted to be the result of an intramolecular oxygen transfer reaction. Treatment of tetra-ortho-tolylporphinatoiron(III) chloride (TTPFeCl) with iodosylbenzene afforded a reactive intermediate which degraded the porphyrin in the absence of a oxidizable substrate. Similar oxidation of tetraphenylporphinatochromium(III) chloride with iodosylbenzene gave a stable intermediate which has been characterized as an oxochromium(V) complex.

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VL - 7

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JO - Journal of Molecular Catalysis

JF - Journal of Molecular Catalysis

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ER -

Hydroxylation and expoxidation reactions catalyzed by synthetic metalloporphyrinates. Models related to the active oxygen species of cytochrome P-450

Abstract

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