Handbook of Reagents for Organic Synthesis, Reagents for Radical and Radical Ion Chemistry

725 Pages·2009·12.073 MB·English

by  David Crich

Handbook of Reagents
for Organic Synthesis
Reagents for Radical and
Radical Ion Chemistry
OTHER TITLES IN THIS COLLECTION
CatalystComponentsforCouplingReactions
EditedbyGaryA.Molander
ISBN9780470518113
Fluorine-ContainingReagents
EditedbyLeoA.Paquette
ISBN9780470021774
ReagentsforDirectFunctionalizationforC–HBonds
EditedbyPhilipL.Fuchs
ISBN0470010223
ReagentsforGlycoside,Nucleotide,andPeptideSynthesis
EditedbyDavidCrich
ISBN047002304X
ReagentsforHigh-ThroughputSolid-PhaseandSolution-PhaseOrganicSynthesis
EditedbyPeterWipf
ISBN047086298X
ChiralReagentsforAsymmetricSynthesis
EditedbyLeoA.Paquette
ISBN0470856254
ActivatingAgentsandProtectingGroups
EditedbyAnthonyJ.PearsonandWilliamR.Roush
ISBN0471979279
AcidicandBasicReagents
EditedbyHansJ.ReichandJamesH.Rigby
ISBN0471979252
OxidizingandReducingAgents
EditedbyStevenD.BurkeandRickL.Danheiser
ISBN0471979260
Reagents,AuxiliariesandCatalystsforC–CBondFormation
EditedbyRobertM.CoatesandScottE.Denmark
ISBN0471979244
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Handbook of Reagents
for Organic Synthesis
Reagents for Radical and
Radical Ion Chemistry
Editedby
David Crich
WayneStateUniversity,Detroit,MI,USA
Thiseditionfirstpublished2008
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LibraryofCongressCataloging-in-PublicationData
Handbookofreagentsfororganicsynthesis.
p.cm
Includesbibliographicalreferences.
Contents:[1]Reagents,auxiliariesandcatalystsforC–Cbond
formation/editedbyRobertM.CoatesandScottE.Denmark
[2]Oxidizingandreducingagents/editedbyStevenD.Burkeand
RiekL.Danheiser[3]Acidicandbasicreagents/editedby
HansJ.ReichandJamesH.Rigby[4]Activatingagentsand
protectinggroups/editedbyAnthonyJ.PearsonandWilliamR.Roush
[5]Chiralreagentsforasymmetricsynthesis/editedbyLeoA.Paquette
[6]Reagentsforhigh-throughputsolid-phaseandsolution-phaseorganic
synthesis/editedbyPeterWipf[7]Reagentsforglycoside,nucleotide
andpeptidesynthesis/editedbyDavidCrich[8]Reagentsfordirect
functionalizationofC–Hbonds/editedbyPhilipL.Fuchs[9]Fluorine-
ContainingReagents/editedbyLeoA.Paquette[10]CatalystComponents
forCouplingReactions/editedbyGaryA.Molander[11]Reagentsfor
RadicalandRadicalIonChemistry/editedbyDavidCrich
ISBN0-471-97924-4(v.1) ISBN0-471-97926-0(v.2)
ISBN0-471-97925-2(v.3) ISBN0-471-97927-9(v.4)
ISBN0-470-85625-4(v.5) ISBN0-470-86298-X(v.6)
ISBN0-470-02304-X(v.7) ISBN0-470-01022-3(v.8)
ISBN978-0-470-02177-4(v.9) ISBN978-0-470-51811-3(v.10)
ISBN978-0-470-06536-5(v.11)
1.Chemicaltestsandreagents. 2.Organiccompounds-Synthesis.
QD77.H371999 98-53088
547’.2dc21 CIP
AcataloguerecordforthisbookisavailablefromtheBritishLibrary.
ISBN13:978-0-470-06536-5
Setin9½/11½ptTimesRomanbyThomsonPress(India)Ltd.,NewDelhi.
PrintedinGreatBritainbyAntonyRowe,Chippenham,Wiltshire.
e-EROS Editorial Board
Editor-in-Chief
LeoA.Paquette
TheOhioStateUniversity,Columbus,OH,USA
ExecutiveEditors
DavidCrich
WayneStateUniversity,Detroit,MI,USA
PhilipL.Fuchs
PurdueUniversity,WestLafayette,IN,USA
GaryA.Molander
UniversityofPennsylvania,Philadelphia,PA,USA

Contents
Preface ix Copper(II)Acetate 195
1,4-Cyclohexadiene 202
Introduction xi Decacarbonyldimanganese 205
(Diacetoxyiodo)benzene 208
SelectedMonographsandReviews 1 DibenzoylPeroxide 217
Acrylonitrile 9 Di-t-butylHyponitrite 228
AllylEthylsulfone 16 1,1-Di-t-butylPeroxide 232
Allyltributylstannane 19 2,2-Di(t-butylperoxy)butane 238
Allyltriphenylstannane 29 Di-t-butylPeroxyoxalate 239
(cid:2)
4,4-Azobis(4-cyanopentanoicacid) 30 N,N-Dichlorobenzenesulfonamide 242
(cid:2)
1,1-Azobis-1-cyclohexanenitrile 32 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 244
(cid:2)
2,2-Azobis(2,4-dimethyl-4-methoxyvaleronitrile) 32 DilauroylPeroxide 256
(cid:2)
2,2-Azobis[2-(2-imidazolin-2-yl)-propane] 1,4:5,8-Dimethano-1,2,3,4,5,6,7,8-octahydro-9,10-
Dihydrochloride 34 dimethoxyanthraceniumHexachloroantimonate 265
Azobisisobutyronitrile 36 (2,6-Dimethoxy-1-methyl-2,5-cyclohexadien-1-yl)
(cid:2)
2,2-Azobis(2-methylpropanimidamide)Dihydrochloride 37 (1,1-dimethylethyl)dimethylsilane 267
Benzeneselenol 39 [2-(Dimethylamino)methyl]phenylDimethyltinHydride 269
BenzenesulfonylAzide 45 2,2-Dimethyl-5-[3-(diphenylstannyl)propyl]-1,
1,2-Benziodoxol-3(1H)-oneDerivatives 48 3-dioxolan-4-one 271
4,5-Bis(1,1-dimethylethyl)-6-ethoxy-2,2-dimethyl-3, DimethylDisulfide 272
7-dioxa-4-aza-6-phosphanonanoicAcid6-oxide 51 5,5-Dimethyl-1-(phenylmethyl)-3-pyrazolidinone 275
Bis(dimethylglyoximato)(methyl)(pyridine)cobalt(III) 53 Dimethyl[3-(1-pyrenyl)propyl]stannane 278
Bis(ethoxythiocarbonyl)sulfide 58 DiphenylDiselenide 279
Bis[(1R,2S,5R)-menthyl](phenyl)tinHydride 60 DiphenylDisulfide 285
Bis[4-(tridecafluorohexyl)phenyl]Diselenide 61 DiphenylDisulfone 288
Bis(trimethylstannyl)Benzopinacolate 63 DiphenylDitelluride 290
BromineAzide 65 Diphenyl[2-(4-pyridyl)ethyl]tinhydride 291
(cid:2) (cid:2)
BromineTrifluoride 66 2,2-DipyridylDisulfideN,N-Dioxide 292
(1-Bromoethenyl)chlorodimethylsilane 72 t-Dodecanethiol 296
(Bromomethyl)chlorodimethylsilane 73 EthanesulfonylAzide 299
N-Bromosuccinimide 79 EthylDifluoroiodoacetate 300
Bromotrichloromethane 89 Galvinoxyl 303
t-ButylHydroperoxide 92 Hexabutyldistannane 305
t-ButylHypochlorite 112 Hexamethyldistannane 307
t-ButylHypoiodite 117 HydrogenBromide 309
t-ButylIsocyanide 119 HydrogenSelenide 311
N-t-Butyl-1-diethylphosphono-2,2-dimethylpropyl N-Hydroxyphthalimide 315
Nitroxide 129 N-Hydroxypyridine-2-thione 321
CarbonMonoxide 133 HypophosphorousAcid 331
CarbonTetrabromide 148 Indium 337
CarbonTetraiodide 150 IodineAzide 353
Catecholborane 152 Iodine–NitrogenTetroxide 358
(cid:2)
Cerium(IV)AmmoniumNitrate 159 2-Iodobiphenyl-2-thiolDimethylaluminumComplex 360
Chlorobis(dimethylglyoximato)(pyridine)cobalt(III) 166 Iodoform 361
N-Chloro-N-cyclohexylbenzenesulfonamide 174 Iodosylbenzene 365
4-(4-Chlorophenyl)-3-hydroxy-2(3H)thiazolethione 175 1-Iodo-2-(2,2,2-triethoxyethyl)benzene 375
Chromium(II)Acetate 179 Iron,Bis(pyridine)bis(2-pyridinecarboxylato-N1,O2) 376
Chromium(II)Chloride 183 Iron(III)Chloride 380
CobaltSalenComplexes 192 Lead(IV)Acetate 389
CobaltSalophenComplexes 194 Lead(IV)Acetate–Copper(II)Acetate 396
viii CONTENTS
Lead(IV)Acetate–Iodine 397 2,2,6,6-Tetramethylpiperidin-1-oxyl 525
(cid:2)
Lithium4,4-Di-t-butylbiphenylide 399 Tetraphenyldiphosphine 531
Lithium1-(Dimethylamino)naphthalenide 403 1,1,2,2-Tetraphenyldisilane 535
LithiumNaphthalenide 404 Tetrathiafulvalene 539
(cid:2)
Manganese(III)Acetate 407 1,1-Thiocarbonylbis(1H-benzotriazole) 544
(cid:2)
Manganese(III)Acetate–Copper(II)Acetate 409 1,1-Thiocarbonyldiimidazole 545
Manganese(III)Acetylacetonate 411 Thionocarbonates 551
Mercury(II)Oxide–Bromine 412 Thiophenol 553
Mercury(II)Oxide–Iodine 413 Thiophosgene 563
MethylAcrylate 415 Titanium(III)Chloride 567
1-Methyl-2-azaadamantaneN-Oxyl 421 O-p-TolylChlorothioformate 570
N-Methylcarbazole 422 Tri(t-butoxy)silanethiol 571
S-MethylN-methyl-N-hydroxydithiocarbamate 424 Tri-n-butyl(iodoacetoxy)stannane 574
N-MethylquinoliniumHexafluorophosphate 426 Tri-n-butylstannane 575
1-[(Methyltelluro)ethyl]benzene 428 Triethylborane 585
MethylThioglycolate 429 Triethylsilane 601
Naphthalene-1,8-diylBis(diphenylmethylium)Perchlorate 433 m-TrifluoromethylbenzoylChloride 609
4-NitrobenzenesulfenylChloride 434 α,α,α-Trifluorotoluene 611
o-Nitrobenzenesulfonylhydrazide 436 Triisopropylsilanethiol 614
Nitroethylene 438 Trimethylstannane 618
Nitrosobenzene 442 Triphenylbismuthine 619
NitrosylChloride 452 Triphenylsilane 620
S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium Triphenylstannane 626
Hexafluorophosphate(HOTT) 455 Tris(2-perfluorohexylethyl)tinHydride 629
4-Pentyne-1-thiol 457 Tris(phenylthio)phosphine 632
PeroxyacetylNitrate 458 Tris(trimethylsilyl)silane 633
PhenylChlorothionocarbonate 460 TritylThionitrite 640
Phenyliodine(III)Dichloride 462 VanadylTrichloride 643
Phenylsulfonylethylene 465 VitaminB 644
12
PhosphinicAcid,AlkylEsters 469 Xenon(II)Fluoride 649
Polymethylhydrosiloxane(PMHS) 473 Ytterbium(II)Chloride 651
PotassiumO-ethylXanthate 478 Ytterbium(III)Trifluoromethanesulfonate&Ytterbium(III)
PotassiumFerricyanide 488 TrifluoromethanesulfonateHydrate 652
3-PyridinesulfonylAzide 492
2-Pyridinethiol 493 ListofContributors 659
Samarium(II)Iodide 499
Se-Phenylp-tolueneselenosulfonate 509 ReagentFormulaIndex 673
SodiumAnthracenide 512
SodiumBis(dimethylglyoximato)(pyridine)cobaltate 513 SubjectIndex 677
SodiumHypophosphite 515
SodiumNaphthalenide 516 GeneralAbbreviations
SulfurylChloride 519