Singlet Oxygen Generation from [Bis(trifluoroacetoxy)iodo]benzene and Hydrogen Peroxide

被引：28

作者：

Catir, Mustafa ^{[1
]}

Kilic, Hamdullah ^{[1
]}

Nardello-Rataj, Veronique ^{[2
]}

Aubry, Jean-Marie ^{[2
]}

Kazaz, Cavit ^{[1
]}

机构：

[1] Ataturk Univ, Dept Chem, Fac Sci, TR-25240 Erzurum, Turkey

[2] ENSCL, CNRS, UMR 8009, Equipe Oxydat & Physicochim Formulat, F-59652 Villeneuve Dascq, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 12期

关键词：

LOW-TEMPERATURE OZONATION; ALKYL HYDROTRIOXIDES ROOOH; TRIOXIDE HOOOH; REACTIVE INTERMEDIATE; ELECTRICAL-DISCHARGE; BUTYL HYDROPEROXIDE; TRANSIENT FORMATION; CHEMICAL GENERATOR; MOLECULAR-OXYGEN; SELF-REACTION;

D O I：

10.1021/jo9007496

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Decomposition of hydrogen peroxide with a hypervalent iodine compound was examined. The results indicate that treatment of a hypervalent iodine compound with hydrogen peroxide produces singlet molecular oxygen (O-1(2)). Convergent evidence for the production of singlet molecular oxygen (O-1(2)) by decomposition of hydrogen peroxide with a hypervalent iodine compound comes from chemical trapping experiments and the specific chemiluminescence detection of O-1(2) at 1270 nm. Substantial evidence demonstrates that hydroperoxyl radical produced from hydrogen peroxide with hypervalent iodine reacts via a tetraoxidane intermediate, decomposing to give singlet molecular oxygen.

引用

页码：4560 / 4564

页数：5

共 59 条

[1] ENZYME-CATALYZED ASYMMETRIC-SYNTHESIS - KINETIC RESOLUTION OF RACEMIC HYDROPEROXIDES BY ENANTIOSELECTIVE REDUCTION TO ALCOHOLS WITH HORSERADISH-PEROXIDASE [J].

ADAM, W ;

HOCH, U ;

LAZARUS, M ;

SAHAMOLLER, CR ;

SCHREIER, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (48) :11898-11901

[2]

[Anonymous], 2003, TOPICS CURRENT CHEM

[3] SEARCH FOR SINGLET OXYGEN IN THE DECOMPOSITION OF HYDROGEN-PEROXIDE BY MINERAL COMPOUNDS IN AQUEOUS-SOLUTIONS [J].

AUBRY, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (21) :5844-5849

[4] ABSOLUTE RATE CONSTANTS FOR HYDROCARBON AUTOXIDATION .33. A PRODUCT STUDY OF THE SELF-REACTION OF ALPHA-TETRALYLPEROXYLS IN SOLUTION [J].

BAIGNEE, A ;

CHENIER, JHB ;

HOWARD, JA .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (09) :2037-2043

[5] PRODUCT STUDIES OF MUTUAL TERMINATION REACTIONS OF SEC-ALKYLPEROXY RADICALS - EVIDENCE FOR NON-CYCLIC TERMINATION [J].

BENNETT, JE ;

SUMMERS, R .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (08) :1377-1379

[6] An Efficient Methyltrioxorhenium(VII)-Catalyzed Transformation of Hydrotrioxides (ROOOH) into Dihydrogen Trioxide (HOOOH) [J].

Bergant, Ana ;

Cerkovnik, Janez ;

Plesnicar, Bozo ;

Tuttle, Tell .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (43) :14086-+

[7] Bis(trifluoroacetoxyiodo)benzene-induced activation of tert-butyl hydroperoxide for the direct oxyfunctionalization of arenes to quinones [J].

Catir, M ;

Kilic, H .

SYNLETT, 2004, (12) :2151-2154

[8]

Catir M, 2003, SYNLETT, P1180

[9] The ozonation of silanes and germanes: An experimental and theoretical investigation [J].

Cerkovnik, J ;

Tuttle, T ;

Kraka, E ;

Lendero, N ;

Plesnicar, B ;

Cremer, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (12) :4090-4100

[10] Evidence for HOOO radicals in the formation of alkyl hydrotrioxides (ROOOH) and hydrogen trioxide (HOOOH) in the ozonation of C-H bonds in hydrocarbons [J].

Cerkovnik, J ;

Erzen, E ;

Koller, J ;

Plesnicar, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (03) :404-409

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