Fuhrhop J., Penzlin G. — Organic Synthesis: Concepts, Methods, Starting materials :: Электронная библиотека попечительского совета мехмата МГУ

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Fuhrhop J., Penzlin G. — Organic Synthesis: Concepts, Methods, Starting materials

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Название: Organic Synthesis: Concepts, Methods, Starting materials

Авторы: Fuhrhop J., Penzlin G.

Язык:

Рубрика: Химия/

Статус предметного указателя: Готов указатель с номерами страниц

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Издание: second edition, rewise and enlarged

Год издания: 1994

Количество страниц: 432

Добавлена в каталог: 29.10.2005

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Предметный указатель

Oligoisoprenes      see “Terpenes”
Oligonucleotides, cationic oligonucleotides      343
Oligonucleotides, hexose nucleotides, “homo-DNA”      344—345
Oligonucleotides, syntheses      215—227
Oligonucleotides, syntheses, 1,3,2-dioxaphosphole method      219
Oligonucleotides, syntheses, combined chemical-enzymatic methods      225—227
Oligonucleotides, syntheses, mutagenic modifications      341—342
Oligonucleotides, syntheses, phosphite methods      219—224 341—343
Oligonucleotides, syntheses, phosphodiester method      216—217
Oligonucleotides, syntheses, phosphotriester method      217—218
Oligonucleotides, syntheses, solid-phase methods      221—224 341—343
Oligonucleotides, syntheses, “sticky end” method      225—226
Oligopeptides      see “Peptides”
Oligosaccharides, syntheses      269—272
Oppenauer oxidation      133—134 278 285
Oppenauer oxidation, epimerization of alcohols by      288
Optical resolution in drug synth.      300—301 309
Optical resolution in natural product synthesis      319—320 327
Optical resolution, enantioselective synthesis, “kinetic resolution”, enzymatic      167 277 278
Optical resolution, enantioselective synthesis, “kinetic resolution”, Noyori hydrogenation      102—103 325—326
Optical resolution, enantioselective synthesis, “kinetic resolution”, Sharpless epoxidation      124—127 264—265 321—325
Organometallic compounds      see “1-Alkynes” or the corresponding metals or metal complexes
Organometallic compounds, metal-metal exchange      5 7
Organometallic compounds, metal-metal exchange with copper(1+)      5 20—21
Organometallic compounds, metal-metal exchange with zinc(2+)      5 46
Organometallic compounds, organyl coupling reactions      36 40—44
Organometallic compounds, preparation, from C-H-acidic compounds      5—9
Organometallic compounds, preparation, from haloalkanes, with alkylUthium      70
Organometallic compounds, preparation, with metals      5—7 17 20 46
Organometallic compounds, reactivity, effect of metal counterions      5 40
ortho-Quinodimethanes = 5,6-bis(alkylidene)-1,3-cyclohexadienes      280—281 297
Orthoformic acid, esters (trimethoxymethane and 1,1',1''-[methylidynetris(oxy)]tris[ethane]), formyl $a^{1}$ -synthon      18 58—59 198
Orthoformic acid, esters (trimethoxymethane and 1,1',1''-[methylidynetris(oxy)]tris[ethane]), Meerwein’s dialkoxymethylium reagents      38 58—59
Orthoformic amides      see “Methanamine ...”
Orthoformic diamides      see “Methanediamine ...”
Osmium(8+) oxide ( $\mathrm{OsO_{4}}$ or $\mathrm{OsO_{4}\cdot2Py}$ ), oxidation of alkenes to 1, 2-diols      81—82 128—129 210 282
Osmium(8+) oxide ( $\mathrm{OsO_{4}}$ or $\mathrm{OsO_{4}\cdot2Py}$ ), oxidation of alkenes to 1, 2-diols, $\mathrm{OsO_{4}}$ -catalysed      82 129 282
Osmium(8+) oxide ( $\mathrm{OsO_{4}}$ or $\mathrm{OsO_{4}\cdot2Py}$ ), oxidation of alkenes to 1, 2-diols, enantioselective      129
Osmium(8+) oxide ( $\mathrm{OsO_{4}}$ or $\mathrm{OsO_{4}\cdot2Py}$ ), toxicity      128
Oxa-Cope (= Claisen) rearrangement      87
Oxacyclotrideca-5,9-dien-2-one, (E,E)-      42
Oxalyl chloride      see “Ethanedioyl dichloride”
Oxazoies, 2-aikyl-4,5-dihydro-, $\alpha$ -alkylation      13 22—23
Oxazoies, 2-aikyl-4,5-dihydro-, enantioselective syntheses with      22—23
Oxazoies, 2-aikyl-4,5-dihydro-, preparation      22—23 153
Oxidation      115—140 (see also “Eliminations oxidative” “Rearrangements oxidative” “Corresponding
Oxidation of $\alpha-\mathrm{CH}$ of ketones      79 121—122 156
Oxidation of alcohols      133—136
Oxidation of alkanes      115—116 118—119 285—286
Oxidation of alkenes      116—117 119—121 123—131
Oxidation of alkenes to 1,2-dihalides      84 118—119 123—124 156—157
Oxidation of alkenes to 1,2-diols      81—82 117 123 127—130 265 276—277
Oxidation of alkenes to 1,2-diols, enantioselective      129
Oxidation of alkenes to haloethers      272 326
Oxidation of alkenes to halohydrins      77 117 275—276 287
Oxidation of alkenes to halolactones      275 319—321 335—336
Oxidation of alkenes to oxiranes (= epoxides)      117
Oxidation of alkenes to oxiranes (= epoxides) by enantioselective Sharpless oxidation      124—127 265 320—325
Oxidation of alkenes to oxiranes (= epoxides) by hydrogen peroxide (2-enones)      275
Oxidation of alkenes to oxiranes (= epoxides) by peracids      117 123—124 156—157
Oxidation of alkenes to oxiranes (= epoxides) via halohydrinations      77 117 287 319—320 327—328
Oxidation of alkenes, allylic oxidation      119—121
Oxidation of alkylarenes      120
Oxidation of alkylboranes with N-oxidcs      37
Oxidation of alkynes      117 131—132
Oxidation of dienes to 2-ene-1,4-diols      124 276—277
Oxidation of hydrazines to diazenes      35 331
Oxidation of phosphines to P-oxides      282
Oxidation of phosphite esters      219—220 223
Oxidation of tert. amines      116 120—121 138—139
Oxidation, remote oxidation      116 118 285—286
Oxidation, table      116—118
Oxidative cleavage, degradation or rearrangement of $\alpha$ -amino acids      48
Oxidative cleavage, degradation or rearrangement of 1,2-arenediol derivatives      87—88
Oxidative cleavage, degradation or rearrangement of 1,2-diols      81—82 88 202 273 292
Oxidative cleavage, degradation or rearrangement of 2-enones      82
Oxidative cleavage, degradation or rearrangement of alkenes      81—82 87—88 202 259 280
Oxidative cleavage, degradation or rearrangement of alkynes      117 132
Oxidative cleavage, degradation or rearrangement of arylsilanes with $\mathrm{Br_{2}}$       80
Oxidative cleavage, degradation or rearrangement of ketones      see “Ketones”
Oxidative cleavage, degradation or rearrangement of oxiranes      88
Oxidative cleavage, degradation or rearrangement of p-methoxybenzyl ethers      157 325—329
Oxidative cleavage, degradation or rearrangement of tert. amines with BrCN      309
Oxidative cleavage, degradation or rearrangement of thioethers      314—315
Oxidative cleavage, degradation or rearrangement of triorganylboranes      47—48 130—131
Oxidative cleavage, degradation or rearrangement of “Ox” protecting groups      164
Oxidative coupling in 1-alkenyl boranes      37—38
Oxidative coupling of 1-alkynes      40 154—155 339
Oxidative coupling of enol silyl ethers      65
Oxidative coupling of phenols      293—295
Oxidative decarboxylations      see “Decarboxylation”
Oxidative p-elimination      see “ $\beta$ -Elimination”
Oxidative sulfitolysis      239—240
Oximes, Beckmann rearr.      136—137
Oximes, heterocycles from      307—308
Oximes, reduction of      98 112
Oxirane (ethylene oxide), $a^{2}$ -synthon      64 149 198 281 300
Oxirane (ethylene oxide), 2, 3-dimethyl-, (R,R)-, synthesis with      64
Oxirane (ethylene oxide), 2-decyl-3-(5-methylhexyl)-, cis- (gipsy moth pheromone), syntheses      34 125
Oxirane (ethylene oxide), 2-ethyl-, alkynylation      64
Oxirane (ethylene oxide), 2-ethyl-, pr.      175
Oxirane (ethylene oxide), 2-methyl- (propylene oxide), alkylation with $\mathrm{R_{2}CuLi}$       21
Oxirane (ethylene oxide), 2-methyl- (propylene oxide), pr.      175
Oxiranes from $\alpha$ -halo ketones by enantioselective reduction      108
Oxiranes from 1,2-diols      160 269 327—328
Oxiranes from 2-enones with $\mathrm{H_{2}O_{2}}$       274—275
Oxiranes from carbonyl compounds      45
Oxiranes from halohydrins      77 117 160 287 319—320 327—328
Oxiranes, $a^{2}$ -synthons      16 44 63—65
Oxiranes, opening with 1-alkynes      64—65 321 325 327—328
Oxiranes, opening with acetate/acetic acid      282
Oxiranes, opening with acids      322
Oxiranes, opening with amines      291
Oxiranes, opening with benzenethiol      265
Oxiranes, opening with carboxylic acid dianions      63
Oxiranes, opening with diorganylcuprates(1-)      21 44 269
Oxiranes, opening with hydrogen fluoride      287
Oxiranes, opening with hydroxide      123—124 265
Oxiranes, opening with imidic ester ec-anions      63—64
Oxiranes, pr.      175
Oxiranes, red. opening      98 114 274—275 319—320
Oxiranes, synthesis from alkenes by Sharpless epoxidation      124—127 265 320—325
Oxiranes, synthesis from alkenes via halohydrinations      77 117 287 319—320 327—328
Oxiranes, synthesis from alkenes with hydrogen peroxide      274—275
Oxiranes, synthesis from alkenes with peracids      117 123—124 156—157
Oxonium, (methoxymethylene)methyl-      see “Methylium dimethoxy-”
Oxonium, triethyl-, O-alkylation of carboxamides      111—112 260
Oxonium, triethyl-, O-alkylation of vinylogous carboxamides      249
Oxonium, triethyl-, S-alkylation of thioethers      39
Oxonium, trimethyl-, methyl $\alpha$ -synthon      16
Oxygen, oxn. of organic anions      19 121
Oxygen, singlet-state, oxidative cleavage of alkenes with      259
Oxygen, singlet-state, [2+4]cycloaddition of      102 276—277
Oxymetazoline      305
Oxyphenbutazone, $(\pm)$ -      305
Oxytetracycline, $(\pm)$ -, total synthesis      318
Ozonolysis of 1,2-arenediol derivatives      87—88
Ozonolysis of alkenes      87—88 156—157 280 285 322 323 326
Ozonolysis of enamines      285
Ozonolysis of enol esters and ethers      87—88 280
Ozonolysis of hydrazones      26
Pagodane, rearr. to dodecahedrane      336
Pagodane, synthesis      336—337
Palladium      see “Hydrogenation” “Hydrogenolysis”
Palladium(0) complexes, $\pi$ -allyl-Pd(0), allylation with      27 164 303
Palladium(0) complexes, $\pi$ -allyl-Pd(0), polymer-bound stereoselective      164 303
Palladium(0) complexes, catalysts for 1,5-enyne cycloisomerization      84
Palladium(0) complexes, catalysts for coupling reactions      42 295
Palladium(0) complexes, catalysts for trimethylenemethane generation      84
Palladium(2+), $\pi$ -allyl complexes from      27

Palladium(2+), catalysts for Heck coupling      42—43
Palladium(2+), catalysts for hydrogen 1,3-shifts      90
Palladium, exhaustive dehydrogenation      139—140 337
Panizzi formylation      58—59
Papaverine alkaloids, conversions      294—295
Papaverine alkaloids, pr.      290
Papaverine alkaloids, syntheses      293
para-Cyclophanes = $tricyclo[8.2.2.2^{4,7}]hexadeca-4,6,10,12,13,15-hexaenes$ , synth.      38—39
PCC      see “Chromate(1-) chlorotrioxo- pyridinium”
PCR = polymerase chain reaction      226—227
Pechmann’s 1,2,3-triazole synthesis      151—152
Penam      311
Penem derivative      32
Penicillanic acid, 6-amino- (6-APA)      311—312
Penicillin derivs., conversion to cephalexins      315
Penicillin derivs., prepn. from penicillin G      311—312
Penicillin derivs., syntheses      32 313—314
Pentanoic acid, 2-ethyl-, retro-synthesis      199—201
Pentanoic acid, 4-oxo- (levulinic acid), cephalosporins from      313—314
Pentanoic acid, 4-oxo- (levulinic acid), indole synthesis from      307
Pentanoic acid, 4-oxo- (levulinic acid), pr.      177
Pentanoic acid, 4-oxo- (levulinic acid), retro-synthesis with      205
Pentanoic acid, 5-bromo-, esters, 5-acylation      47
Pentanoic acid, 5-bromo-, esters, pr.      180
Pentazocine, (-)-, synthesis      309
Pentonic acids, esters, 2-hexulosides from      272
Peptides, activation of carboxylate      143—146 230—241
Peptides, genetic engineering methods      241—246
Peptides, protection of functional groups      161—165 229
Peptides, racemization, prevention of      145 231—232
Peptides, solid-phase methods      232—237 241
Peptides, solution (= liquid-phase) methods      237—241
Peptides, synthesis      228—246
Peracetic acids      see “Ethaneperoxoic acids”
Peracids      see “Carboperoxoic acids”
Perbenzoic acids      see “Benzenecarboperoxoic acids”
Perchloric acid      Li salt Diels—Alder 86
peri-Substituents, crowding of      see “Steric strain”
Pericyclic reactions      see “ $\beta$ -Eliminations pyrolytic”
Pericyclic reactions, aldol type reactions      59—62
Pericyclic reactions, carbonyl allylations      67—69
Pericyclic reactions, hydride shift from alkylborane to ketone      108
Pericyclic reactions, Moflatt — Pfitzner oxn.      133
Pericyclic reactions, oxidations with $\mathrm{SeO_{2}}$       119 122
Pericyclic reactions, Reformatsky reactions      44—45
Periodate ( $\mathrm{IO_{4}^{-}}$ ) or periodic acid ( $\mathrm{H_{5}IO_{6}}$ ), oxidation of phenylselenyl groups      139
Periodate ( $\mathrm{IO_{4}^{-}}$ ) or periodic acid ( $\mathrm{H_{5}IO_{6}}$ ), oxidative cleavage of $\alpha$ -hydroxy ketones      62
Periodate ( $\mathrm{IO_{4}^{-}}$ ) or periodic acid ( $\mathrm{H_{5}IO_{6}}$ ), oxidative cleavage of 1,2-diols      81—82 272—273 282 292
Periodate ( $\mathrm{IO_{4}^{-}}$ ) or periodic acid ( $\mathrm{H_{5}IO_{6}}$ ), oxidative cleavage of 1,2-diones      137
Periodate ( $\mathrm{IO_{4}^{-}}$ ) or periodic acid ( $\mathrm{H_{5}IO_{6}}$ ), oxidative cleavage of oxiranes      88
Periodinane reagent, Dess — Martin      134 328—329
Permanganate, potassium, ox. cleavage of ketones      137
Permanganate, potassium, oxidation with, of $\alpha$ -CH of carboxylic acids      120—121
Permanganate, potassium, oxidation with, of alkenes      128
Permanganate, potassium, oxidation with, of alkynes      117 132
Permanganate, potassium, oxidation with, of benzylic CH      120
Peroxide, hydrpgen      see “Hydrogen peroxide”
Peroxymolybdenum complex      see “Molybdenum”
Peterson olefination      28 33—34
PG      see “Prostaglandins”
Phase-transfer catalysts      see “Benzenemethanaminium ...” “Butanaminium ...” “18-Crown-6”
Phenazopyridine      306
Phenols via ortho-alkylation and rearr.      319—320
Phenols, derivatives, O-arlyation (copper-catalysed)      295
Phenols, derivatives, oxidative C-C and C-N coupling      293—294
Phenols, derivatives, palladation and coupling reactions      42—43
Phenols, para-alkylation of      93
Phenothiazines, synthesis      309—310
Phenyl      see “Benzene ...”
Phenylalanine, N-acyl-D- or -L-, synth.      102—103
Phenylbutazone      305
Phenylephrine, (-)-(R)-      301
Phenylpropanolamine, $(\pm)$ -      302
Pheromones, synth., by Peterson olefination      34
Pheromones, synth., by Wiuig olefination      31
Phlorins      258
Phosphate esters      see “Phosphoric acid esters”
Phosphine oxides, deoxygenation with $\mathrm{SmI_{2}}$       115
Phosphine oxides, synthesis, alkyl halide + $\mathrm{Ph_{2}PLi}$       282
Phosphine oxides, Wittig — Horner type olefination with      281
Phosphine, 1,2-ethanediylbis[diphenyl- (Diphos), chelation of Pd(2+)      27
Phosphine, diphenyl-, Li salt, $S_{N}$ with      282
Phosphine, tributyl-, stabilization of organylcopper      277
Phosphine, triphenyl-, P-aikylation of      17 32
Phosphine, triphenyl-, palladium complex catalysts      27 42 295
Phosphine, triphenyl-, reagent with iodine, OH/I exchange      328
Phosphine, triphenyl-, reagents with diazenedicarboxylic esters, Mitsunobu reactions with      160—161 286
Phosphine, triphenyl-, reagents with N-halosuccinimides, conversion of alcohols to halides      169
Phosphine, triphenyl-, reagents with tetrahalomethanes, conversion of prim, alcohols to halides      266
Phosphine, triphenyl-, sulfur extrusion with, from disulfides      39
Phosphine, triphenyl-, sulfur extrusion with, from thiiranes      35 59—60 334
Phosphine, triphenyl-, thioesters from disulfides      146 319—320
Phosphine, [1,1'-binaphthalene]-2,2'-diylbis[diphenyl- (Binap), (R)- and (S)-, chiral Noyori hydrogenation catalysts from      102—103
Phosphite esters      see “Phosphorous acid esters”
Phospholipid membranes      350
Phosphonic acid, (diazomethyl)-, dialkyl ester, methylidynation of aldehydes to 1-alkynes      325
Phosphonic acid, 1,3-propanediylbis[-, cyclizn. with      334
Phosphonic acid, alkyl-, dialkyl esters, Horner olefinations by      29 30 267 272—273
Phosphonic acid, alkyl-, dialkyl esters, pr.      188
Phosphonic acid, alkyl-, dialkyl esters, relative reactivity      28—29
Phosphonic acid, diesters, oxidative amidation to phosphoramidates      343
Phosphonic diamide, P-ethyl-N,N,N',N'-tetramethyl-, alkylation and olefination      327—329
Phosphonium ylides      6—7 28—32
Phosphonium ylides, olefination with      see “Phosphonium ...”
Phosphonium ylides, olefination with, relative reactivities      28—29
Phosphonium ylides, olefination with, Z-selectivity and mechanism      28—31
Phosphonium ylides, reaction with triorganylboranes      9
Phosphonium, (1,3-propanediyl)bis[triphenyl-, cyclizations with      334
Phosphonium, (1-methylethyl)triphenyl-      283 322
Phosphonium, (2-methoxy-2-oxoethyl)triphenyl-, pr.      188
Phosphonium, (2-methoxy-2-oxoethyl)triphenyl-, Wittig reaction      32—33
Phosphonium, (2-oxoethyl)triphenyl-, monosaccharide homologization by      264—265
Phosphonium, (2-oxoethyl)triphenyl-, pr.      188
Phosphonium, (4-carboxybutyl)triphenyl-, pr.      188
Phosphonium, (4-carboxybutyl)triphenyl-, prostaglandin synthon      7 272—273 275—276
Phosphonium, (alkoxymethyl)triphenyl-, formyl $d^{1}$ -synthons      6—7 18 48—49
Phosphonium, (alkoxymethyl)triphenyl-, pr.      188
Phosphonium, alkyltriphenyl-, alkylidene d-synthons      7 31—32 201 203
Phosphonium, alkyltriphenyl-, pr.      188
Phosphonium, ethenyltriphenyl-, diene additions to      85
Phosphonium, ethyltriphenyl-, pr.      188
Phosphonium, ethyltriphenyl-, Wittig reaction      283
Phosphonium, hexyltriphenyl, pr.      188
Phosphonium, hexyltriphenyl, Wittig reaction      321
Phosphonium, methyltriphenyl-, pr.      188
Phosphonium, methyltriphenyl-, Wittig reaction      31—32
Phosphonium, pentyltriphenyl-, pr.      188
Phosphonium, pentyltriphenyl-, Wittig reaction      31
Phosphonium, triphenyl[1-(phenylthio)cyclopropyl]-, $a^{3}$ -synthon for cyclopentanellations      16 83
Phosphonium, [3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenyl]triphenyl-, (all-E)- (” $\mathrm{C_{20}}$ salt”)      31
Phosphonium, [3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl]triphenyl-, (E,E)      31
Phosphonium, [thiobis(methylene)]bis[triphenyl-, cyclizations with      334
Phosphoramidate-linked oligonucleotides      343
Phosphoramidite method, oligonucleotide synthesis      220—224 341—343
Phosphorane, pentachloro-      see “Phosphorus(5+) chloride”
Phosphoranes, (alkylideneazino)-      see “Ketones (triphenylphosphoranylidene)hydrazones”
Phosphoranes, alkylidene-      see “Phosphonium ...”
Phosphoric acid, 4-chlorophenyl ester, nucleoside coupling with      217—218
Phosphoric acid, esters      see “Nucleotides”
Phosphoric acid, esters, prepn. by Mitsunobu type reaction      160—161
Phosphoric triamide, hexamethyl- (HMPTA, HMPA) in Mimoun’s Mo complex      121—122
Phosphoric triamide, hexamethyl- (HMPTA, HMPA), reducing agent $\mathrm{SmI_{2}/(Me_{2}N)_{3}PO}$       115
Phosphorodichloridous acid, 2,2,2-trichloroethyl ester, nucleoside coupling with      220
Phosphorous acid, esters, Mitsunobu type reactions with      160—161
Phosphorous acid, esters, oxidation of      219—220 223 342 343
Phosphorous acid, esters, red. cleavage of 1,3-dioxolane-2-thiones      142
Phosphorous acid, esters, reduction with, of 1,2-dione via 1,3,2-dioxaphosphole      219
Phosphorous acid, esters, reduction with, of hydroperoxides      121
Phosphorous acid, esters, sulfur extrusion from thiiranes      35 59—60 261
Phosphorous acid, esters, sulfur extrusion from thioethers by UV irradiation      39

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