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Taticchi A., Frinquelli F. — The Diels-Alder Reaction: Selected Practical Methods
Taticchi A., Frinquelli F. — The Diels-Alder Reaction: Selected Practical Methods



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Íàçâàíèå: The Diels-Alder Reaction: Selected Practical Methods

Àâòîðû: Taticchi A., Frinquelli F.

Àííîòàöèÿ:

The Diels-Alder reaction mechanism was first reported in 1928 and in the last 70 years has become one of the most commonly used and studied methodologies in organic chemistry. The reaction, which involves the addition of a diene to an alkene to form a six-membered ring, is particularly important in the synthesis of compounds of practical interest such as drugs, dyes, polymers, fragrances, agrochemicals and fine chemicals. The experimental procedure is very simple with generally good yields and minor side reactions. The use of organic solvents is not always necessary - an important factor when considering greener synthetic options. This book focuses on practice, describing procedures and techniques and as well as reporting on industrial applications. Graphical illustration presents the concepts in a clear and concise format, covering procedures and techniques employed to realize selective and clean syntheses based on the Diels-Alder methodology.


ßçûê: en

Ðóáðèêà: Õèìèÿ/

Ñòàòóñ ïðåäìåòíîãî óêàçàòåëÿ: Ãîòîâ óêàçàòåëü ñ íîìåðàìè ñòðàíèö

ed2k: ed2k stats

Ãîä èçäàíèÿ: 2002

Êîëè÷åñòâî ñòðàíèö: 356

Äîáàâëåíà â êàòàëîã: 29.03.2009

Îïåðàöèè: Ïîëîæèòü íà ïîëêó | Ñêîïèðîâàòü ññûëêó äëÿ ôîðóìà | Ñêîïèðîâàòü ID
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Ïðåäìåòíûé óêàçàòåëü
Diels — Alder reactions of acylnitroso compounds      172t
Diels — Alder reactions of surfactant reagents      174—176
Diels — Alder reactions, base-catalyzed      190
Diels — Alder reactions, biocatalyst-promoted      180—185
Diels — Alder reactions, catalyzed      144 185—190 261—267
Diels — Alder reactions, cationic      128—130
Diels — Alder reactions, consecutive      2 20 21
Diels — Alder reactions, diastereoselective      199 244 255t
Diels — Alder reactions, domino      2 20 198
Diels — Alder reactions, enantioselective      135 289
Diels — Alder reactions, high pressure      205—249 267
Diels — Alder reactions, inorganic solid-surface-promoted      143—149
Diels — Alder reactions, ionic      5—10 192 200 295
Diels — Alder reactions, Lewis acid catalyzed      99—142
Diels — Alder reactions, micelle-promoted      174—179
Diels — Alder reactions, microwave-assisted      158—163 195 196
Diels — Alder reactions, multiple      20—22
Diels — Alder reactions, normal      122—123
Diels — Alder reactions, pericyclic      4—5 12
Diels — Alder reactions, photo-induced      163—169
Diels — Alder reactions, radical      5—10
Diels — Alder reactions, regioselectivity of      12 22 23—24 148 175 176 198 288t
Diels — Alder reactions, repetitive      245
Diels — Alder reactions, retro      15—18 35 261 290
Diels — Alder reactions, stereoselectivity      24—25
Diels — Alder reactions, tandem      20 21
Diels — Alder reactions, thermal      5 29—98 162 176 214
Diels — Alder reactions, ultrasound-assisted      154—158 195
Diels — Alder reactions, uncatalyzed      252—261
Diels — Alder reactions, using resin-anchored reagents      149—153
Diels-Alderase      181 184
Dienes      2 3 15 16 25 148
Dienes, across-ring      64—66
Dienes, acyclic      36 102
Dienes, heterocyclic      40—42 110—112
Dienes, inner-outer ring      49—64 219—223
Dienes, inner-ring      191 223—236
Dienes, open chain      29—37 191 208—217
Dienes, outer-ring      43—48 217—219
Dienes, stereochemistry of substituents      24
Dienes, sulfinyl groups and      112—114
Dienes, surfactant      176
Dienes, tropones as      226—229
Dienes, unsymmetric      10 23
Dienophiles      3—4 5 8 12 15 44 67 101
Dienophiles, acetylenic      43 49 57
Dienophiles, carbonyl-containing      109 115
Dienophiles, heterocyclic      106—108
Dienophiles, imino      137
Dienophiles, olefinic      43
Dienophiles, reactions with dienes      191
Dienophiles, reactivity of neutral      9
Dienophiles, stereochemistry of      25
Dienophiles, sulfinyl groups and      112—114
Dienophiles, surfactant      176
Dienophiles, unsymmetric      10 23
Diethyl fumarate      170 173 285
Diethyl maleate      285
Diethylaluminum chloride      126
Dihydro-4-pyridones      187
Dihydrocannivonine      262
Dihydropyranes      123 124
Dihydropyranones      37
Dihydropyrans      122
Dihydropyridines      239
Dihydropyridinones      240
Dihydropyrones      90
Dihydrothiopyrans      123
Dihydrovinylphenanthrenes      55 221
Diiodosamarium      110
Diisopropylethylamine      224
Dimethyl formamide      191
Dimethyl fumarate      8 32 43 44 99
Dimethylacetylenedicarboxylate      32 34 40 49 50 111 127 159
Dimethylaluminum selenide      71
Dimethylamine      69 79
Dimethylaminobutadiene      31
Dimethylcyclobutane      102
Dimethylcyclopropane      102
Dimethylmaleate      32 44 279
Dimethyltetrahydroindenone      223
Dipyridyltetrazine      81
Diterpenes      154 212 232
Divinylbenzene      115
Divinylnaphthalenes      52
Dodecane sulfonates      177
Dodecyl maltoside      174
Dodecyl sulfates      177
Electrogenerated acid (EGA)      192
Electron-withdrawing groups      34 71
Enaminoketones      69 240
Enantioselection      117 135 243 289
Endo adducts      171 174 177 184 190 191 208 209
Endo diastereoselectivity      36 117
Endo selectivity      74 83 192 228 266 276
Endo/exo diastereoselectivity      15 178 179 236 280 288
Enolethers      124 126 237
Epibatidine      90 238
ethane      284
Ethene      4 5 12 29 62
Ethyl acetylenedicarboxylate      260
Ethyl acrylate      32 170 279 285
Ethyl-4-methyl-3,5-hexadienoate      255
ethylene      29 284
Ethylene glycol      278
Ethylpropiolate      34
Ethylvinylether      208
Ethyne      172 227
Ethynyltributyltin      68 91
Exo addition      14 63 145
Exo adducts      15 40 174 184 228 276
Facial stereoselectivity      49 73 83 292
Feringa-butenolide      74
Ferrocenium hexafluorophosphate      114
Flavones      85 89
Fluoboric acid      187
Fluorophenols      33
FMO theory      12 15 22 23 24 57
Formaldehyde      261
Friedel — Crafts reactions      279
Fullerene [C60]      36 84 87 168 224 241
Fullerene [C60], condensed aromatics and      193 200
Fullerene [C60], derivatization of      35 67
Fullerene [C60], o-quinodimethanes and      46 47
Fumaric acid      149
Fumaronitrile      8
Functional groups, protection of      252
Furan      57 113 148 170 252 269
Furanamide      272
Furanones      40
Furans      40 58 89 112 229—234 267
Furfuryl fumarates      239
Furylaldehydes      149 151
Glucopyranosil-1,3-pentadiene      260
Glyoxal      158 258
Glyoxylic acid      185 258 264 265 294
graphite      160 161 196
Grub’s ruthenium initiator      152
Guanidinium chloride      252 253
Helicenebisquinones      219
Helicenes      55 56
Hematoporphyrin      163 169
Hetero-Diels — Alder reactions      34 66—73 83 122—126 158
Hetero-Diels — Alder reactions in supercritical $CO_{2}$      287
Hetero-Diels — Alder reactions with heterodienophiles      213—214
Hetero-Diels — Alder reactions, asymmetric      131 133 238
Hetero-Diels — Alder reactions, intermolecular      240
Hetero-Diels — Alder reactions, intramolecular      79 82 171 292
Heterocycles      57 72 82 149 213
Heterodienes      66—70
Heterodienophiles      66 70—73 213—217
Hexadecyltrimethylammonium bromide      282
High-speed vibration milling (HSVM)      193
Homo      22 29 57 62 67 107
Homo-Diels — Alder reactions      18—20 126—128
Homobarrelenones      226 227
Hydrindanones      101
Hydrobenzosuberone      76 101
Hydrofluorenones      104
Hydrophenanthrenones      212
Hydroxamic acid      257
Iceane      81
Imino Diels — Alder reactions      134 270
Indanone      53 227
Inden-1-one      53 56 221
Indeno[c]phenanthrenones      53
Indium trichloride      134 266 293
Indole      44 63 164
Indolquinolines      9
Intermolecular Diels — Alder reactions      1 3 116 205 240 278
Intermolecular Diels — Alder reactions, aqueous      290
Intermolecular Diels — Alder reactions, Lewis acid catalysis      128
Intramolecular Diels — Alder reactions      1 3 8 74—83
Intramolecular Diels — Alder reactions of amino acid-derivative trienes      149
Intramolecular Diels — Alder reactions of franj-cycloalkenones      91
Intramolecular Diels — Alder reactions of furans      170 197 232
Intramolecular Diels — Alder reactions of furfuryl fumarates      239
Intramolecular Diels — Alder reactions of polyenones      270
Intramolecular Diels — Alder reactions, high pressure      233
Intramolecular Diels — Alder reactions, immonium ion based      291
Intramolecular Diels — Alder reactions, microwave-assisted      163
Intramolecular Diels — Alder reactions, tandem photooxidation      196
Inverse electron-demand Diels — Alder reactions      3 4 23 123—125 126 208
Inverse electron-demand Diels — Alder reactions, 2-pyrones and      234
Inverse electron-demand Diels — Alder reactions, heterocycles and      68
Inverse electron-demand Diels — Alder reactions, intermolecular      216
Inverse electron-demand Diels — Alder reactions, Lewis acid catalyzed      109
Iodine      191
Ionic liquids      278—281
Iron (III) 2-ethylhexaonate      124
Isomerization      14 107 279
Isooctane      282
Isoprene      6 104 108 115 187 287 288
Isoprene, 4-isopropyl-2-cyclehexenone      102
Isoprene, but-3-en-2-one and      279
Isoprene, catalysts and      118
Isoprene, dimethyl acetylenedicarboxylate and      274
Isoprene, maleic anhydride and      286
Isoprene, Nafion-Hand      189
Isoprene, quinidine-5,8-dione and      106
Isoprene, zeolites and      148 194
Isoquinoline-5, 8-dione      106
Isoquinolines      70 106 197
Jatropholone A and B      232
Jencks postulate      184
JV-phenylmaleimide      80 195 226 236 245 276
JV-phenylmaleimide, 1-oxa[4.4.4]propella-5, 7-diene and      224
JV-phenylmaleimide, Lewis acid catalysis      73
JV-phenylmaleimide, methyl palustrate and      243
JV-phenylmaleimide, microwave-assisted reactions      161
K-10 montmorillonite      143 144 145 146 161
Ketals      271 274
Ketodeoxyheptulosonic acid      259
Ketones      63 109 271 274
L-abrine      266
l-menthylallyl-ether      38
Lactams      191 200
Lactones      45 271
Lanthanide shift reagent-catalysis      126
Lanthanide triflates      108 109 110 251 262 264 293
Lawesson’s reagent      69
Lewis acid catalysts      37 206 209 214 268 288
Lewis acid catalysts, alkoxybutadienes and      73
Lewis acid catalysts, exo-endo diastereoselectivity      15
Lewis acid catalysts, high pressure and      205
Lewis acid catalysts, norbornene derivatives and      38
Lewis acid catalysts, olefinic acetals and      199
Lewis acid catalysts, quinone-mono-ketals      212
Lewis acid catalysts, surfactant combined      176 177
Lewis acid catalysts, zeolites and      148 194
Lewis acids      23 24 99—142 191 230
Lewis acids in ionic liquids      279—281
Lewis acids, (-)-menthol-aluminum      147
Lewis acids, coupling photolysis      167
Lewis acids, Lanthanide triflates      293
Lewis acids, water-tolerant      251
Lithium chloride      252 253
Lithium perchlorate      113 295 296
Lithium perchlorate-diethyl ether (LP-DE)      268—273 294
Lithium perchlorate-nitromethane      273—274 295
Lithium trifluoromethanesulfonimide      274—276 296
LUMO      22 23 24 36 107
Macrocycles      217 242
Maleic acid      149
Maleic anhydride      80 145 151 164 224 243
Maleic anhydride and      160 163
Maleic anhydride, 1,3-cyclohexadiene and      287
Maleic anhydride, 2-methoxy-1,3-butadiene and      117
Maleic anhydride, 2-vinylthiophene and      58
Maleic anhydride, anthracene and      99 157 160 163
Maleic anhydride, C-2 vinyl glical and      49
Maleic anhydride, cyclopentadiene and      14 164
Maleic anhydride, furan and      230 231 252
Maleic anhydride, isoprene and      286 288
Maleic anhydride, norboradiene and      18
Maleic anhydride, polycycles synthesis      43 81
Maleic anhydride, tropone and      226
Maleimide      116 117 230
Maleonitrile      8
Malic acid      258
Mannich conditions      290
Menthylacrylate      38 145
Metal ions, influence of      265
Methacrolein      133 147 259
Methanol      8 104 155 255
Methoxy carbonyl maleic anhydride      231
Methoxy cyclohexadiene      180
Methoxytrimethylsilane      6 128 129
Methyl acrylate      8 32 43 44 235 287
Methyl acrylate, 2-pyrone and      235
Methyl acrylate, cyclopentadiene and      117 147 178 255 280 282 283t 286
Methyl acrylate, ionic liquids and      280
Methyl acrylate, sulfinyldiene and      113
Methyl acrylate, zeolites and      148
Methyl cis-dihydrojasmonate      38
Methyl methacrylate      123
Methyl palustrate      243
Methyl propynoate      62
Methyl tanshinonate      195
Methyl vinyl ketone      144 156 170 255 266
Methyl vinyl ketone, 2-methoxy-3-thiophenylbutadiene      12
Methyl vinyl ketone, cyclopentadiene and      252
Methyl-5-aminofuroate      86
Methyl-trans-4-methoxy-2-oxo-3-butenoate      216
Methylalumoxane      134
Methylamine hydrochloride      264
Methylbenzoquinone      269
Methylglyoxylate      72 158
Methylpropiolate      117
Methylrhenium trioxide      266
Mevinolin      123
Micelles      283
Michael reactions      7 268
Microemulsion      281—283
MMX force field calculations      62
Monosaccharides      214
Morpholinoacrylonitrile      197
N,N-diethyltryptamine-N-oxide      63
N,N-dimethylacylamide      184
N-acryloyl oxazolidones      133 190
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