_ü Table of Contents

Preface V

Introduction 1

Acetyl Nitrate and Other Acyl Nitrates 7 Alkyl Nitrites 9 Ammonium Cerium(IV) Nitrate and Other Cerium(IV) Salts 11 Ammonium Peroxydisulfate 20 Barium Dihydroxytrioxoruthenate(VI) and Other Dihydroxytrioxoruthenate(VI) Salts 24 Barium Ferrate(VI) and Other Ferrate(VI) Salts 26 Barium Manganate(VI) and Other Manganate(VI) Salts 29 Benzeneseleninic Acid and Related Reagents 33 Benzeneseleninic Anhydride and Related Reagents 36 Benzo-1,4-quinone 40 Bis(acetylacetonato)oxovanadium(IV) 47 Bis(trimethylsilyl) Peroxide 51 [Bis(trifluoroacetoxy)iodo]benzene 56 Bromine 61 N-Bromoacetamide 74 /V-Bromosuccinimide 76 tert-Butyl Hydroperoxide 81 tert-Butyl Hypochlorite and Other Alkyl Hypochlorites 95 Cetyltrimethylammonium Permanganate and Other Quaternary Ammonium Permanganates 102 Chloramine-T and Related Reagents 105 o-Chloranil and Other Benzo-1,2-quinones 107 p-Chloranil 111 Chlorine 117 Chlorochromate Reagents 124 3-Chloroperoxybenzoic Acid 129 N-Chlorosuccinimide 143 Chromate Esters 147 149 Chromium(IV) Oxide 156 Chromium(VI) Oxide 158 Chromium(VI) Oxide-Nitrogen Hetarene Complexes 162 Chromyl Chloride 166 Cobalt(lll) Salts 168 Corey-Kim Reagent 170 Cumene Hydroperoxide 173 Dess-Martin Periodinane 177 (Diacetoxyiodo)benzene 183 Diacyl Peroxides and Acyl Alkyl Peroxides 191 2,3-Dichloro-5,6-dicyanobenzo-1,4-quinone 196 3,3-Dimethyldioxirane 210

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A/,A/-Dimethyl-4-nitrosoaniline 223 Dimethyl Sulfoxide 225 233 Fluorochromate Reagents 235 Halooxovanadium(V) Reagents 237 Peroxide 240 1-Hydroxy-1,2-benziodoxol-3(1H)-one and Other 1-Oxy-1,2?i3-benziodoxol-3(1H)-ones 278 1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-Oxide 282 [Hydroxy(tosyloxy)iodo]benzene 288 Hypofluorous Acid 293 lodic Acid, lodate Salts, and Diiodine Pentoxide 296 Iodine 299 /V-lodosuccinimide 314 lodosylbenzene 317 lodylbenzene 324 Iron(lll) Chloride 327 Iron(lll) Nitrate 336 Lead(IV) Acetate 340 Lead(IV) Oxide 358 Manganese(lll) Acetate 365 Manganese(IV) Oxide 368 Mercury(ll) Acetate and Other Mercury(ll) Salts 385 Mercury(ll) Oxide 390 Methyl Hypobromite 396 4-Methylmorpholine /V-Oxide 398 3-Methyl-3-(trifluoromethyl)dioxirane 402 Methyltrioxorhenium(VII) 407 Molybdenum(V) Chloride 412 Monoperoxycamphoric Acid 414 Monoperoxyphthalic Acid and Magnesium Monoperoxyphthalate 416 Nickel Peroxide 421 426 Nitric Oxide 433 3-Nitrobenzenesulfonic Acid 435 Nitrogen Dioxide 437 Nitronium Tetrafluoroborate and Other Nitronium Salts 442 2-Nitropropane 444 Nitrosonium Tetrafluoroborate and Other Nitrosonium Salts 446 Nitrosyl Chloride 449 Nitrous Oxide 451 Osmium(VIII) Oxide 453 Oxaziridines and Oxaziridinium Salts 461 Oxodiperoxomolybdenum(VI)-Pyridine-HexamethylphosphoricTriamideand Related Reagents 467 Oxone 471 479 Palladium(ll) Acetate 493 Palladium(ll) Chloride 499 Table of Contents IX

Peracetic Acid 504 Perbenzoic Acid and Related Reagents 511 514 Performic Acid 516 Perhydrates and Other a-Hydroperoxy Heteroatom Compounds 518 521 Permanganate Salts of Metals Other Than Potassium 525 Peroxymaleic Acid 529 531 Peroxysulfonic, Peroxyseleninic, and Peroxyphosphinic Acids 534 Polyoxometalar.es 536 Potassium Dichromate, Dichromate, and Other Metal Dichromates 539 Potassium Hexacyanoferrate(lll) 546 Potassium Nitrosodisulfonate 553 Potassium Osmate(VI) 558 Potassium Permanganate 564 Potassium Peroxydisulfate and Other Metal Peroxydisulfates 581 Potassium Superoxide 585 Pyridine 1 -Oxide and Derivatives 588 Pyridinium Chlorochromate 591 Pyridinium Dichromate and Other Dichromate Salts with Nonmetallic Cations 597 Pyridinium Tribromide and Other Ammonium Tribromides 603 Rhenium(VII) Oxide 606 Ruthenium(VIII) Oxide 608 Selenium Dioxide 616 Silver(l) Carbonate 622 Silver(l) Chromate 626 Silver(l) Oxide 628 Silver(ll) Oxide and Other Silver(ll) Compounds 635 Singlet 639 and Other Bromate Salts 648 Sodium Bromite 652 Sodium Chlorite 654 658 and Other Hypochlorite Salts 663 Sodium Nitrite 671 Sodium Perborate 676 Sodium Percarbonate 681 Sodium Periodate 684 Sodium Tungstate and Tungstophosphates 691 Sulfur Trioxide 698 Sulfuryl Chloride 700 Tetrabutylammonium Periodate and Related Reagents 705 Tetrabutylammonium Peroxydisulfate and Related Reagents 707 2,2,6,6-Tetramethylpiperidin-1 -oxyl and Related Reagents 709 Tetrapropylammonium Perruthenate 714 Thallium(lll) Nitrate and Related Reagents 719 Thionyl Chloride 723 Table of Contents

Trichloroisocyanuric Acid 726 Trifluoroperoxyacetic Acid 730 Trimethylamine N-Oxide 735 Triphenylcarbenium Salts 740 Urea- Adduct 748 Vanadium(V) Oxide 752

Name Index 755

Formula Index 761

Reaction Classification Index 765

Abbreviations 779