The Chemistry of Peroxides. Volume 2

1510 Pages·2006·23.123 MB·English

by  Rappoport Z. (ed.)

The chemistry of
peroxides
Thechemistryofperoxides,volume2
Edited by Z. Rappoport  2006 John Wiley & Sons, Ltd ISBN: 0-470-86274-2
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O O
The chemistry of
peroxides
Volume 2
Part 1
Editedby
ZVI RAPPOPORT
TheHebrewUniversity,Jerusalem
2006
AnInterscience Publication
The chemistry of
peroxides
Volume 2
Part 2
Editedby
ZVI RAPPOPORT
TheHebrewUniversity,Jerusalem
2006
AnInterscience Publication
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Contributing authors
Waldemar Adam Instituteof Organic Chemistry, Universityof Wu¨rzburg,
am Hubland, D-97094 Wu¨rzburg, Germany and
Department of Chemistry, University of Puerto Rico, Rio
Piedras, Puerto Rico 00931,USA. Fax: [phone];
e-mails: [email protected] and
[email protected]
WataruAndo Department of Chemistry, University of Tsukuba,
Tennodai, Tsukuba, Ibaraki 305–8577,Japan. Fax: +81
29 851 4796; e-mail: [email protected]
Wilhelm J. Baader InstitutodeQu´ımica,UniversidadedeSa˜oPaulo-Av.Prof.
Lineu Prestes, 748 Bl., 12S CEP 05508-900,Sa˜o
Paulo—SP, Brazil. Fax: [phone]; e-mail:
[email protected]
Robert D.Bach Department of Chemistry and Biochemistry, University of
Delaware, Newark, Delaware 19716,USA. Fax: +1 302
831 6335; e-mail: [email protected]
Mario D.Bachi Department of Organic Chemistry, The Weizmann
Instituteof Science, Rehovot 76100, Israel. Fax: +972
8934 4142; e-mail: [email protected]
ErickL. Bastos InstitutodeQu´ımica,UniversidadedeSa˜oPaulo-Av.Prof.
Lineu Prestes, 748 Bl., 12S CEP 05508-900,Sa˜o
Paulo—SP Brazil. Fax: [phone]; e-mail:
[email protected]
AlbrechtBerkessel Department of Organic Chemistry, University of Cologne,
Greinstr. 4, D-50939 Koln, Germany. Fax: [phone]
5102; e-mail: [email protected]
Olga Bortolini Dipartimento di Chimica, Universita` della Calabria, Via
Bucci, cubo 12C, I-87036 Rende (CS), Italy, Fax: +39
098 449 3307; e-mail: [email protected]
JeanCadet Laboratoire ‘Le´sions des Acides Nucle´iques’,
◦
LCIB-UMR-E n 3 CEA-UJF, De´partement de Recherche
Fondamentale sur la Matie`re Condense´e, CEA/Grenoble,
F-38054 Grenoble Cedex 9, France. Fax: [phone]
5090; e-mail: [email protected]
Giovanni Cerioni DipartimentoFarmaco ChimicoTecnologico,Universita` di
Cagliari, Via Ospedale72, I-09124, Cagliari, Italy. Fax:
[phone]; e-mail: [email protected]
vii
viii Contributingauthors
James Chadwick Department of Chemistry, The Robert Robinson
Laboratories,University of Liverpool, Liverpool,L69
7ZD, UK. Fax: [phone]
ValeriaConte Dipartimento di Scienze e TecnologieChimiche,
Universita` di Roma “Tor Vergata”, via della Ricerca
Scientifica, I-00133 Roma, Italy. Fax: [phone];
e-mail: [email protected]
PaoloDiMascio Departamento de Bioqu´ımica, Institutode Qu´ımica,
Universidadede Sa˜o Paulo, Ar. Prof. Lineu Prestes, 748
CP 26077,CEP 05513-970,Sa˜o Paulo, SP, Brazil. Fax:
[phone]; e-mail: [email protected]
JensHartung Fachbereich Chemie, Organische Chemie, Technische
Universita¨tKaiserslautern, Erwin-Schro¨dinger-Straße,
D-67663 Kaiserslautern,Germany. e-mail:
[email protected]
Vidyadhar Jadhav Center for Molecular Design and Synthesis, Department
of Chemistry, Korea Advanced Instituteof Science and
Technology,Taejon 305-701, Korea. Fax: [phone]
5818
SungSooKim Department of Chemistry, Inha University,Incheon
402-751,South Korea. Fax: [phone]; e-mail:
[email protected]
YongHaeKim Center for Molecular Design and Synthesis, Department
of Chemistry, Korea Advanced Instituteof Science and
Technology,Taejon 305-701, Korea. Fax: [phone]
5818; e-mail: [email protected]
EdwardE.Korshin Department of Organic Chemistry, The Weizmann
Instituteof Science, Rehovot 76100, Israel. Fax: +972
8934 4142; e-mail: [email protected]
JoelF.Liebman Department of Chemistry and Biochemistry, University of
Maryland,Baltimore County, 1000 Hilltop Circle,
Baltimore, MD 21250, USA. Fax: [phone];
e-mail: [email protected]
FrancescaMocci Dipartimento di Scienze Chimiche, Universita` di Cagliari,
CittadellaUniversitariadi Monserrato,SS 554 Bivio per
Sestu, I-09024, Monserrato (CA), Italy
PaulM. O’Neill Department of Chemistry, The Robert Robinson
Laboratories,University of Liverpool, Liverpool,L69
7ZD, UK. Fax: [phone]; e-mail:
[email protected]
MichaelOrfanopoulos Department of Chemistry, Universityof Crete, G-71409
Iraklion,Greece. Fax: [phone]; e-mail:
[email protected]
MinYoungPark Center for Molecular Design and Synthesis, Department
of Chemistry, Korea Advanced Instituteof Science and
Technology,Taejon 305-701, Korea. Fax: [phone]
5818
SarahL. Rawe Department of Chemistry, The Robert Robinson
Laboratories,University of Liverpool, LiverpoolL69
7ZD, UK. Fax: Fax: [phone]
Contributingauthors ix
SuzanneW.Slayden DepartmentofChemistry,GeorgeMasonUniversity,4400
University Drive, Fairfax, VA 22030-4444,USA. Fax: +1
703 993 1055; e-mail: [email protected]
Cassius V.Stevani InstitutodeQu´ımica,UniversidadedeSa˜oPaulo-Av.Prof.
Lineu Prestes, 748 Bl., 10S CEP 05508-900,Sa˜o
Paulo—SP, Brazil. Fax: [phone]; e-mail:
[email protected]
Manolis Stratakis Department of Chemistry, University of Crete, G-71409
Iraklion, Greece. Fax: [phone]
IngridSvoboda Fachgebiet Strukturforschung, FB 11, Material-und
Geowissenschaften, TechnischeUniversita¨t Darmstadt,
Petersenstr. 23, D-64287 Darmstadt, Germany. e-mail:
[email protected]
AlexeiV.Trofimov Instituteof Biochemical Physics, Russian Academy of
Sciences, ul. Kosygina4, Moscow 119991,Russian
Federation and Instituteof Organic Chemistry, University
of Wu¨rzburg, am Hubland,D-97094 Wu¨rzburg, Germany.
Fax: [phone]; e-mail: avt [email protected]
Nadine Vogl Department of Organic Chemistry, University of Cologne,
Greinstr. 4, D-50939 Koln, Germany. Fax: [phone]
5102; e-mail: [email protected]
Georgios C. Department of Chemistry, University of Crete, G-71409
Vougioukalakis Iraklion, Greece.
Fax: [phone]
JacobZabicky Institutes for Applied Research and Department of
Chemical Engineering, Ben-Gurion University of the
Negev, Beer-Sheva 84105, Israel. Fax: [phone];
e-mail: [email protected]
Cong-Gui Zhao Department of Chemistry, University of Texas at San
Antonio,San Antonio,TX 78249,USA. Fax: [phone]
7428; e-mail: [email protected]
Foreword
The earlier volume in The Chemistry of Functional Groups dealing with organic com-
pounds including the O−O functional group in peroxides, hydroperoxides and related
groups was edited by S. Patai and published in 1983. In the intervening 23 years there
have been significant advances in the field, some of which are covered in books such
as W. Ando’s Organic Peroxides, Wiley (1992), and some were covered in chapters in
Patai’s Supplement E2 (1993).
The present volume comprises 17 chapters, written by 27 authors from 11 countries,
and deals with theoretical aspects and structural chemistry of peroxy compounds, with
theirthermochemistry,17ONMRspectraandanalysis,extensivelywithsynthesisofcyclic
peroxides and with the uses of peroxides in synthesis, and with peroxides in biological
systems. Heterocyclic peroxides, containing silicon, germanium, sulfur and phosphorus,
as well as transition metal peroxides are treated in several chapters. Special chapters
deal with allylic peroxides, advances in the chemistry of dioxiranes and dioxetanes, and
chemiluminescence of peroxide and with polar effects of their decomposition. A chapter
on anti-malarial and anti-tumor peroxides, a hot topic in recent research of peroxides,
closes the book.
Unfortunately,twoplannedchaptersdidnotmaterialize,onpolyoxidesandonstructural
chemistryoforganometallicandheteroatomicperoxides.Theliteraturecoverageismostly
up to the end of 2004.
Iwouldbegratefultoreaderswhodrawmyattentiontomistakesinthepresentvolume,
or to the omission of chapters which deserve to be included in such a treatise.
ZVI RAPPOPORT
Jerusalem,
October 2005
xi