Gif chemistry: New Evidence for a Non-radical Process

U Schuchardt; MJDM Jannini; David Trevor Richens; MC Guerreiro; EV Spinace

doi:10.1016/S0040-4020(01)00147-8

Gif chemistry: New Evidence for a Non-radical Process

U Schuchardt, MJDM Jannini, David Trevor Richens, MC Guerreiro, EV Spinace

School of Chemistry

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

Abstract

When performed under a nitrogen monoxide atmosphere, Gif oxidation of cyclohexane with hydrogen peroxide gives no changes in activity or selectivity, showing that tripler oxygen is neither formed nor required in the oxidation. Gif oxidation of cis- and trans-decalin occurs preferentially at secondary positions giving high yields of ketones. Oxidation of tertiary positions is as low as approximately 5% and probably involves free radicals. Oxidation of cyclohexane in the presence of mannitol gives no significant loss of activity, showing that OH radicals are not involved in Gif oxidation. Based on these results the mechanism of Gif oxidation is discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	2685-2688
Number of pages	4
Journal	Tetrahedron
Volume	57
DOIs	https://doi.org/10.1016/S0040-4020(01)00147-8
Publication status	Published - 2 Apr 2001

Keywords

catalytic oxidation
Gif chemistry
NO atmosphere
D-mannitol
cis-decalin
trans-decalin
SATURATED-HYDROCARBONS
HYDROGEN-PEROXIDE
OXIDATION
MECHANISM
FUNCTIONALIZATION
CYCLOHEXANE
ALKANES
SYSTEM
H2O2

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title = "Gif chemistry: New Evidence for a Non-radical Process",

abstract = "When performed under a nitrogen monoxide atmosphere, Gif oxidation of cyclohexane with hydrogen peroxide gives no changes in activity or selectivity, showing that tripler oxygen is neither formed nor required in the oxidation. Gif oxidation of cis- and trans-decalin occurs preferentially at secondary positions giving high yields of ketones. Oxidation of tertiary positions is as low as approximately 5% and probably involves free radicals. Oxidation of cyclohexane in the presence of mannitol gives no significant loss of activity, showing that OH radicals are not involved in Gif oxidation. Based on these results the mechanism of Gif oxidation is discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.",

keywords = "catalytic oxidation, Gif chemistry, NO atmosphere, D-mannitol, cis-decalin, trans-decalin, SATURATED-HYDROCARBONS, HYDROGEN-PEROXIDE, OXIDATION, MECHANISM, FUNCTIONALIZATION, CYCLOHEXANE, ALKANES, SYSTEM, H2O2",

author = "U Schuchardt and MJDM Jannini and Richens, {David Trevor} and MC Guerreiro and EV Spinace",

year = "2001",

month = apr,

day = "2",

doi = "10.1016/S0040-4020(01)00147-8",

language = "English",

volume = "57",

pages = "2685--2688",

journal = "Tetrahedron",

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publisher = "Elsevier",

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TY - JOUR

T1 - Gif chemistry: New Evidence for a Non-radical Process

AU - Schuchardt, U

AU - Jannini, MJDM

AU - Richens, David Trevor

AU - Guerreiro, MC

AU - Spinace, EV

PY - 2001/4/2

Y1 - 2001/4/2

N2 - When performed under a nitrogen monoxide atmosphere, Gif oxidation of cyclohexane with hydrogen peroxide gives no changes in activity or selectivity, showing that tripler oxygen is neither formed nor required in the oxidation. Gif oxidation of cis- and trans-decalin occurs preferentially at secondary positions giving high yields of ketones. Oxidation of tertiary positions is as low as approximately 5% and probably involves free radicals. Oxidation of cyclohexane in the presence of mannitol gives no significant loss of activity, showing that OH radicals are not involved in Gif oxidation. Based on these results the mechanism of Gif oxidation is discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

AB - When performed under a nitrogen monoxide atmosphere, Gif oxidation of cyclohexane with hydrogen peroxide gives no changes in activity or selectivity, showing that tripler oxygen is neither formed nor required in the oxidation. Gif oxidation of cis- and trans-decalin occurs preferentially at secondary positions giving high yields of ketones. Oxidation of tertiary positions is as low as approximately 5% and probably involves free radicals. Oxidation of cyclohexane in the presence of mannitol gives no significant loss of activity, showing that OH radicals are not involved in Gif oxidation. Based on these results the mechanism of Gif oxidation is discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

KW - catalytic oxidation

KW - Gif chemistry

KW - NO atmosphere

KW - D-mannitol

KW - cis-decalin

KW - trans-decalin

KW - SATURATED-HYDROCARBONS

KW - HYDROGEN-PEROXIDE

KW - OXIDATION

KW - MECHANISM

KW - FUNCTIONALIZATION

KW - CYCLOHEXANE

KW - ALKANES

KW - SYSTEM

KW - H2O2

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U2 - 10.1016/S0040-4020(01)00147-8

DO - 10.1016/S0040-4020(01)00147-8

M3 - Article

SN - 0040-4020

VL - 57

SP - 2685

EP - 2688

JO - Tetrahedron

JF - Tetrahedron

ER -

Gif chemistry: New Evidence for a Non-radical Process

Abstract

Keywords

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