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

ed2k: ed2k stats

Издание: second edition, rewise and enlarged

Год издания: 1994

Количество страниц: 432

Добавлена в каталог: 29.10.2005

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Предметный указатель

Ferrate(2-), tetracarbonyl-, formyl d-synthon      18 46—47 198
Ferrate(2-), tetracarbonyl-, redn. of acid anhydrides and halides with      46—47
Ferrate(3-), hexakis(cyano-C)-, potassium ( $\mathrm{K_{3}Fe(CN)_{6}}$ ), $\mathrm{OsO_{4}}$ -catalysed oxn. with      129
FGA, retro-synthetic      195
FGI      95
FGI, retro-synthetic      195
FGR, retro-synthetic      195
Fischer formula, erythro/threo definition      62 360
Fischer’s indole synthesis      151—152 296 307
Fischer’s porphyrin synthesis      256
FK 506, total synthesis      324—329
Fluoride, hydrogen, cleavage with, of diol acetonides      277
Fluoride, hydrogen, cleavage with, of silyl ethers      277 328 329
Fluoride, hydrogen, cleavage with, of silyl thioethers      169
Fluoride, potassium, base cat. for Michael addn.      71
Fluoride, silver, halide/fluoride exchange      269—270
Fluoride, tetrabutylammonium, cleavage of silyl ethers      157 159 270 272 281 339
Fluorination with $\mathrm{Et_{2}NSF_{3}}$ (DAST), OH/F exchange      269—270 272
Fluorination with $\mathrm{Et_{2}NSF_{3}}$ (DAST), SR/F exchange ( $\mathrm{Et_{2}NSF_{3}/NBS}$ )      269—270
Fluorination with $\mathrm{F_{2}}$ , oxidation of alkanes      118—119 157
Fluorosulfuric acid, methyl ester      338
Formaldehyde, hydroxymethyl $a^{1}$ -synthon      18 198 203 302
Formaldehyde, Mannich reactions      57 292 300 304 310 317—318
Formaldehyde, reduction of aldehydes with      302
Formaldehyde-sulfoxylate      see “Methanesulfinic acid hydroxy-”
Formamides, N,N-diaikyl-, formyl $a^{1}$ -synthons      16 18 198 255
Formic acid, azido-      see “Carbonazidic acid”
Formic acid, chloro-      see “Carbonochloridic acid”
Formic acid, esters, formyl $a^{1}$ -synthons      18 58—59 155—156 337
Formic acid, esters, orthoesters      see “Orthoformic acid esters”
Formylation, $a^{1}$ -synthons      16 18
Formylation, $a^{1}$ -synthons, formic esters      59 155—156
Formylation, $a^{1}$ -synthons, orthoformamidic esters      79 82
Formylation, $a^{1}$ -synthons, orthoformic esters/trifluoroborane      59
Formylation, $d^{1}$ -synthons      6—8 18
Formylation, $d^{1}$ -synthons, (dichloromethyl)lithium      51—52
Formylation, $d^{1}$ -synthons, 1,3-dithianes      17—18 198 267
Formylation, $d^{1}$ -synthons, allyl or vinyl d-synthons + $\mathrm{O_{3}}$       90
Formylation, $d^{1}$ -synthons, boranes + carbon monoxide      47—48
Formylation, $d^{1}$ -synthons, cyanide anion      50
Formylation, $d^{1}$ -synthons, DMSO anion      51
Formylation, $d^{1}$ -synthons, isocyanomethyl sulfones (TosMIC)      49 51
Formylation, $d^{1}$ -synthons, nitromethane anion      65—66
Formylation, $d^{1}$ -synthons, tetracarbonylferrate(2-)      46—47
Formylation, reductive, (alkoxymethylene)phosphoranes      6 49
Fragmentation reactions      89—90 141—142
Frater — Seebach alkylation      27 325—326
Friedel — Crafts acylation, 1-oxoalkylium (acylium) ions in      15—16
Friedel — Crafts acylation, aldol type cyclizations by      81
Friedel — Crafts alkylation of dipyrromethenes      256—257
Friedel — Crafts alkylation of indoles      291
Friedel — Crafts alkylation of polystyrene      233
Friedel — Crafts alkylation, alkylium ions in      15—16
Fullerenes      357
Fullerenes, metal inclusion compounds      357
Fulvalene      see “Bi-2
Functional group addition (FGA), rerro-synthetic      195
Functional group interconversion (FGI)      95—169
Functional group interconversion (FGI), retro-synthetic      195
Functional group removal (FGR), retro-synthetic      195
Functional group, definition      1—4 50
Furan, Diels — Alder addition to      86 93
Furosemide      305
Gene cloning      241—246
Genetic engineering methods      225—227 241—246
Geraniol      see “2 3
Geranyl bromide      see “2 1-bromo-3
Gipsy moth pheromone      34 125
Girgnard tranform, retro-synthetic      194
Glaser coupling      40
Glass, porous, solid support      221 342
Glucal derivatives      268
Glucosamine, pr.      263
Glucosamine, synthesis      268
Glucose derivatives, pr.      263—264
Glucose derivatives, syntheses of      266—269
Glucose derivatives, syntheses starting from      267—273
Glutethimide, $(\pm)$ -      304
Glycals      268
Glycine, N-benzoyl, $\mathrm{CO^{2-}}$ synthon      48
Glycols      see “Diols”
Glycosyl fluorides      269—270 272
Glycosyl halides, $\beta$ -elimination, 2-acetoxyglycals      268
Glycosyl halides, glycosylations with      267 269—271
Glycosyl halides, prepn.      266 269—270 272
Glycosyl halides, reductive $\beta$ -elimination, glycals      268
Glycosyl imidates      270—271
Glycosylations      267 269—272
Glyoxylic acid = oxoacetic acid, derivs., deblocking of acetals with      328—329
Glyoxylic acid = oxoacetic acid, derivs., pr.      176
Glyoxylic acid = oxoacetic acid, derivs., synthesis      202
Grignard reagents      see “Magnesium alkylhalo-”
Griseofulvin, $(\pm)$ -, synthesis      74
Griseofulvin, dehydro-, $(\pm)$ -, synthesis      86
Guanidine group, protection in arginine      229
Hafnium, $dichlorobis(\eta^{5}-cyclopentadienyl)$ -, + $\mathrm{Ag^{+}}$ , activation of glycosyl fluorides      270
Haloalkanes, alkenes from      see “ $\beta$ -Elimination”
Haloalkanes, alkyl a-synthons      15—16 22—27
Haloalkanes, conversion to phosphines      282
Haloalkanes, conversion to thiols      169
Haloalkanes, coupling of      19—20 36
Haloalkanes, metalation (= umpolung)      5—7 17 20 70 75 326—327
Haloalkanes, reduction of      97 113—115 203
Haloalkanes, reduction of, with alkali metals/ $\mathrm{Bu^{t}OH}$ (Birch redn.)      337
Haloalkanes, reduction of, with chromium(2 +) acetate      286
Haloalkanes, reduction of, with hydrogen/Raney Ni      287
Haloalkanes, reduction of, with methyllithium/lithium bromide      75
Haloalkanes, reduction of, with tributylstannane      97 114—115 275 319—320
Haloalkanes, reduction of, with zinc or zinc-copper      83 335—336
Haloalkanes, synthesis from alcohols, bromination, conc. aq. $\mathrm{Br/PBr_{3}}$       303
Haloalkanes, synthesis from alcohols, chlorination, N-Chlorosuccimmide/ $\mathrm{Ph_{3}P}$       169
Haloalkanes, synthesis from alcohols, chlorination, N-Chlorosuccimmide/ $\mathrm{Ph_{3}P}$ , fluorination with $\mathrm{Et_{2}NSF_{3}}$       269—270 272
Haloalkanes, synthesis from alcohols, chlorination, N-Chlorosuccimmide/ $\mathrm{Ph_{3}P}$ , glycosyl halides      266 269—270 272
Haloalkanes, synthesis from alcohols, chlorination, N-Chlorosuccimmide/ $\mathrm{Ph_{3}P}$ , iodides via tosylates      203 281
Haloalkanes, synthesis from alcohols, chlorination, N-Chlorosuccimmide/ $\mathrm{Ph_{3}P}$ , iodides, iodine/ $\mathrm{Ph_{3}P}$       328
Haloalkanes, synthesis from alcohols, chlorination, N-Chlorosuccimmide/ $\mathrm{Ph_{3}P}$ , Mitsunobu reactions with $\mathrm{ZnX_{2}}$       160—161
Haloalkanes, synthesis from alcohols, chlorination, N-Chlorosuccimmide/ $\mathrm{Ph_{3}P}$ , tetrahalomethane/ $\mathrm{Ph_{3}P}$       266 355
Haloalkanes, synthesis from alcohols, chlorination, N-Chlorosuccimmide/ $\mathrm{Ph_{3}P}$ , thionyl chloride ( $\mathrm{SOCl_{2}}$ )      32
Haloalkanes, synthesis from alcohols, chlorination, N-chlorosuccinimide      282
Haloalkanes, synthesis from alcohols, chlorination, synthesis from thioethers      269—270
Halohydrins (vic-halo alcohols), synthesis of, from 1,2-diols      160 327—328
Halohydrins (vic-halo alcohols), synthesis of, from alkenes      77 117 275—276 287
Halohydrins (vic-halo alcohols), synthesis of, from oxiranes, with HF      287
Halolactonization      275 319—321 335—336
Hauser’s rule      9 24 204
HBT = 1-hydroxy-1H-benzotriazole      145 231
Heck coupling (alkene + organyl halide)      42—43
Hectane, synthesis      36
Helicate complexes      345—346
Hemiacetals, cyclic, from lactones ( $\mathrm{Bu^{i}_{2}AlH}$ )      105 321 322 327—328
Heterocycles      see “Alkaloids” “Drugs” “N-Heterocycles”
Heterocycles, 3-membered      see “Aziridines” “Oxiranes” “Thiiranes”
Heterocycles, macrocyclic      see “Macrocycles”
Hexamethyldisilazane      see “Stlanamine ...”
Hexanoic acid, 2-methyl-, (S)-, synth.      22—23
Hexonamides, N-alkyl-, aqueous suspensions, various micellar aggregates      352—353
High-dilution methods, macrocycle syntheses by      145—146 240—241 329 338
Hindrance, steric      see “Steric hindrance”
Hippuric acid      see “Glycine N-benzoyl-”
HMDS      see “Silanamine ...”
HMPA = HMPTA      see “Phosphoric triamide hexamethyl-”
HOBT = 1-hydroxy-1H-benzotriazole      145 231
Hofmann degradation      139 308 331
Hofmann type elimination of ammonium compounds      57 72 138 140—141 331
Hofmann type elimination of sulfonium compounds      38 338
Hofmann type elimination of sulfoxides      65 86 315
Homo-DNA      344—345
homo-Michael-type additions, $a^{3}+d^{0}$       69—70
homo-Michael-type additions, $a^{4}$ + alkenyl d      276
Homoenolate synthons      14—15 70 76

Horner olefination      28—30 (see also “Phosphonic acids alkyl- diesters”)
Huenig base      see “1-Naphthalenamine N
Huenig bases, polymeric = aminated chloromethylated ethenylbenzene homopolymers, deprotonation with, of ketones      11
Huenig bases, polymeric = aminated chloromethylated ethenylbenzene homopolymers, deprotonation with, or phosphonium salts      32
Huenig bases, polymeric = aminated chloromethylated ethenylbenzene homopolymers, removal of acids with      32
Hybrid plasmids      243—245
hydration      see “Alkenes” “Alkynes”
Hydrazine, hydrazinolysis with, of esters      239—240 331
Hydrazine, hydrazinolysis with, of phthaloyl-protected amines      162 163
Hydrazine, reduction of ketones with      97—98 109
Hydrazines, cyclic, oxn. $\mathrm{N_{2}}$ extrusion      35 331
Hydrazones, aryl-, indole synth. with      151—152 296 307
Hydrazones, dialkyl-, lithiated, alkylation      12 18 25—26
Hydrazones, dialkyl-, lithiated, alkylation, enantioselective (SAMP-hydrazones)      25—26
Hydrazones, dialkyl-, lithiated, ozonolysis of      26
Hydrazones, Wolff — Kishner redn. of      109
Hydrazones, [(4-methylphenyi)sulfonyl]- (tosylhydrazones), fragmentation of      89 141—142
Hydrazones, [(4-methylphenyi)sulfonyl]- (tosylhydrazones), reduction of, to alkanes      109
Hydrazones, [(4-methylphenyi)sulfonyl]- (tosylhydrazones), reduction of, to alkenes      141—142
Hydrides of Al, B, Sn      see “Aluminum” “Aluminate” “Borane” “Borate” “Stannane”
Hydrides, alkali, deprotonation with, of alcohols      23 33 157 325 328
Hydrides, alkali, deprotonation with, of carbonyl compounds      15 49 58 63 93
Hydrides, alkali, deprotonation with, of carboxamides      314
Hydrides, alkali, deprotonation with, of indoles      307
Hydrides, alkali, deprotonation with, of phosphonic diesters      29 334
Hydrides, alkali, deprotonation with, of sulfonium salts      38 45
Hydrides, alkali, deprotonation with, of sulfoxides      6 51
Hydrides, alkali, deprotonation with, of tosylhydrazones      35
Hydroalkylation of alkenes      37 105
Hydroalkylation of alkynes      37—38
Hydroboration      see “Alkenes” “Alkynes”
Hydrobromic acid (aq. HBr), OH/Br exchange (aq. $\mathrm{HBr/PBr_{3}}$ )      303
Hydrobromic acid (aq. HBr), porphyrin synthesis with      255 349
Hydrobromination of alkynes with Zr      132 325
Hydrochlorothiazide      310
Hydrofluoric acid (aq. HF), deblocking with, of diol acetonides      277
Hydrofluoric acid (aq. HF), deblocking with, of silyl ethers      277 329
Hydrofluoric acid (aq. HF), deblocking with, of silyl thioethers      169
Hydroformylation of alkenes      46—48
Hydrogen peroxide, epoxidation with, of 2-enones (with KOH)      274—275
Hydrogen peroxide, epoxidation with, of alkenes (with HCOOH)      123
Hydrogen peroxide, oxidation with, of phenylselenyl groups      139
Hydrogen peroxide, oxidation with, of phosphines to P-oxides      282
Hydrogen peroxide, oxidative cleavage of 2-enones      82
Hydrogen peroxide, oxidative cleavage of phosphorus ylides      31
Hydrogen peroxide, oxidative cleavage or triorganylboranes      47—48 130—131 325
Hydrogen peroxide, oxidative rearr. (Baeyer — Villiger) of carbonyl compounds with $\mathrm{SeO_{2}/H_{2}O_{2}}$       136—137
Hydrogen shift, sigmatropic      262 289 295 “Rearrangements sigmatropic”)
Hydrogenation      96—105 (see also “Hydrogenolysis”)
Hydrogenation of alkenes      41 96—97 101—103 278 283
Hydrogenation of alkynes to (Z)-alkenes      40 64 100—101
Hydrogenation of arenes      87 347
Hydrogenation of heteroarenes      112—113 303
Hydrogenation of iminium ions      293
Hydrogenation of nitroalkanes      66 112 297
Hydrogenation, catalysts, heterogeneous      96 100—102 105 111—113
Hydrogenation, catalysts, homogeneous      96—97 102—103 326
Hydrogenation, catalysts, homogeneous, chiral (Noyori)      102—103 325—326
Hydrogenation, mechanism      101—102
Hydrogenolysis      113—114 (see also “Reductive cleavage”)
Hydrogenolysis of activated keto groups      109
Hydrogenolysis of allylic alcohol derivs.      113—114 312—313
Hydrogenolysis of benzyl carbamates      143 162—163 229 240
Hydrogenolysis of benzyl ethers      157—159 161 271 328
Hydrogenolysis of benzylidene acetals      268
Hydrogenolysis of cyclopropane rings      105
Hydrogenolysis of haloalkanes      97 113—114 286—287
Hydrogenolysis of oxirane rings      113—114 319—320
Hydrogenolysis of thioethers      26 113—114
Hydrogenolysis of “Ox”-protected amines      161 164
hydrolysis      see “Deblocking”
Hydrolysis, enantiotoposelective      167—168 276—277
Hydroperoxide, 1,1-dimethylethyl ( $\mathrm{Bu^{t}OOH}$ , tert-butyl hydroperoxide, TBHP), Sharpless epoxidation with      124—127 265 321—325
Hydrostannylation of alkynes      321
Hydroxamic acid chlorides = N-hydroxy carboximidoyl chlorides      153
Hydroxides, alkali, deprotonation with, of alcohols      157 159 265
Hydroxides, alkali, deprotonation with, of dicarbonyl type compounds      10 71—73
Hydroxides, alkali, deprotonation with, of hydrazones      109
Hydroxides, alkali, deprotonation with, of ketones      69 78 79 82 280
Hydroxides, alkali, deprotonation with, of oxosulfonium salts      8
Hydroxides, alkali, deprotonation with, of sulfonium salts      79 336
Hydroxides, benzyltrimethylammonium      see “Benzene-methanaminium ...”
Hydroxy acids, chiral, pr.      176 183 185 191
Hydroxylamine-HCl, cleavage of acetonides      323
Hydrozirconation of alkynes      132 325
Hyperconjugation effects of alkyl groups on Baeyer — Villiger rearr.      136—137
Hyperconjugation effects of alkyl groups on enolate formation      11—13 57—58 93
Hyperconjugation effects of alkyl groups on relative reactivities of aldehydes vs. ketones to d-synthons      56
Hyperconjugation effects of alkyl groups on relative reactivities of alkenes to oxidation      87—88 123—124 156—157
Hyperconjugation effects of alkyl groups on relative reactivities of prim. vs. sec. alcohols to oxidation      135
Hypochlorites, $\mathrm{RuO_{4}}$ -catd. oxidation of alkynes      132
Hypochlorites, chlorohydrination with      117
Hypochlorus acid, 1,1-dimethylethyl ester, oxidative cleavage of thioethers with      314
Hypochlorus acid, 1,1-dimethylethyl ester, oxidative rearr. of 1-amino alcohols      77—78
Hypoiodites, acyl-, oxn. of alkenes with      127
Imidazoles, synthesis      151—152 305
Imides      see “Dicarboximides”
Imidic acids      see “Carboximidic acids”
Imido esters      see “Carboximidic acids esters”
Imidogens      see “Nitrenes”
Imines, N-alkyl- = N-alkylidene amines, hydrolysis of      57
Imines, N-alkyl- = N-alkylidene amines, N-acylation of      153
Imines, N-alkyl- = N-alkylidene amines, reduction of      112—113
Imines, N-alkyl- = N-alkylidene amines, synthesis of, by condensation of reactive $\mathrm{CH_{2}}$ with nitroso compounds      308
Imines, N-alkyl- = N-alkylidene amines, synthesis of, by trapping of diallylnickel complexes with isocyanides      41
Imines, N-alkyl-, lithiated      12 18 56—57 199
Imines, N-alkyl-, lithiated, directed aldol condensation with      56—57
Imines, synthesis of, aldehyde + amine      298
Imines, synthesis of, alkylation or reduction of nitriles      298—299
Iminium (= N-alkyl-N-alkylidene alkanaminium = immonium) ions (Mannich reagents), aminomethylation with, of 1-alkynes      57
Iminium (= N-alkyl-N-alkylidene alkanaminium = immonium) ions (Mannich reagents), aminomethylation with, of carboxamides      317—318
Iminium (= N-alkyl-N-alkylidene alkanaminium = immonium) ions (Mannich reagents), aminomethylation with, of indoles and phenols      291—292
Iminium (= N-alkyl-N-alkylidene alkanaminium = immonium) ions (Mannich reagents), aminomethylation with, of ketones      57 300 304
Iminium (= N-alkyl-N-alkylidene alkanaminium = immonium) ions (Mannich reagents), aminomethylation with, of pyrroles      252
Iminium (= N-alkyl-N-alkylidene alkanaminium = immonium) ions (Mannich reagents), aminomethylation with, of sulfonamides      310
Iminium (= N-alkyl-N-alkylidene alkanaminium = immonium) ions (Mannich reagents), conversion to enamines      13 88 139
Iminium (= N-alkyl-N-alkylidene alkanaminium = immonium) ions (Mannich reagents), preparation, from carbonyl compounds      13 57 292 300 304 310 318
Iminium (= N-alkyl-N-alkylidene alkanaminium = immonium) ions (Mannich reagents), preparation, oxidation of tert. amines      116 120—121 138—139
Immunosuppressive agent “FK 506”      324—329
Indoles, 2-substitution, Friedel — Crafts type      291
Indoles, 2-substitution, Mannich type      292
Indoles, 2-substitution, Vilsmeier type      293
Indoles, N-acylation      307
Indoles, synthesis (Fischer)      151—152 296 307
Indomethacin      307
INOC = [(4-pyridinylmethoxy)carbonyl)]      241
Inserted DNA sequences      243—245
Insulin B-chain, chemical synthesis      239—240
Insulin, synth. by genetic engineering      244—245
Introns      242
Inversion of configuration      see “Epimerization”
Inversion of configuration of alcohols (Mitsunobu reaction)      160—161 286
Inversion of configuration of alkyl halides or sulfonates by 1,3-dithiane anions      22
Inversion of configuration of alkyl halides or sulfonates by organylcuprates      36
Inversion of configuration of alkyl halides or sulfonates by tetracarbonyIferrate(2-)      46—47
Inversion of configuration of alkyl halides or sulfonates, in triorganylborane rearr.      37—38
Inversion of configuration of allylic acetates with Pd      27 164
Inversion of configuration of allylpalladium with d-synthons      27 264
Inversion of configuration of glycosides with free 2-OH by DAST      272
Inversion of configuration of glycosyl halides      271
Inversion of configuration of oxiranes by 1-alkyne anions      64 204
Inversion of configuration of oxiranes by enolate type anions      63—64
Inversion of configuration of oxiranes by internal alcoholate addition      265
Inversion-esterification of alcohols      160—161 286
Iodide, hydrogen, porphyrin synthesis with      255
Iodine = diiodine ( $\mathrm{I_{2}}$ ) + $\mathrm{Pb(OAc)_{4}}$ , ox. decomp. of RCOOH      337
Iodine = diiodine ( $\mathrm{I_{2}}$ ) + carboxylic acids, oxidation of alkenes to 1,2-diols      127—128
Iodine = diiodine ( $\mathrm{I_{2}}$ ) + hydroxide, rearr. of 1-alkenyl boranes      37
Iodine = diiodine ( $\mathrm{I_{2}}$ ) + triphenylphosphine, OH/I exchange      328
Iodine = diiodine ( $\mathrm{I_{2}}$ ) + water, oxn. of phosphites      219—220 223

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