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

Iodine = diiodine ( $\mathrm{I_{2}}$ ), $Z\rightarrow E$ isomerization of polyenes      31
Iodine = diiodine ( $\mathrm{I_{2}}$ ), iodoetherification with      272 326
Iodine = diiodine ( $\mathrm{I_{2}}$ ), iodolactonization with      321 335—336
Iodine = diiodine ( $\mathrm{I_{2}}$ ), oxidative cleavage of organylzirconium      132
Iodine, phenylbis(trifluoroacetato)- + methanol (Stork reagent), 1,3-dithiane cleavage      328—329
Iodoalkanes      see “Haloalkanes”
Iodoetherification      272 326
Iodolactones      see “Halolactones”
Ion-exchange resins      see “Benzene ethenyl-” “Sulfonic
Ionone, $\alpha$ - or $\beta$ -, pr.      191
Ionone, $\alpha$ - or $\beta$ -, synthesis      90—91
Ionone, $\psi$ -, acid-catalysed cyclization of      90—91
Ipc (isopinocampheyl), chiral auxiliary group      108
Ireland — Claisen rearrangement      87 325
Iron(1+), $dicarbonylethene(\eta^{5}-cyclopentadienyl)$ -, addition of carbon nucleophiles      44
Iron(1+), $tricarbonyl(\eta^{5}-cyclohexadienyi)$ -, addition of carbon nucleophiles      44
Iron, $tricarbonyl(\eta^{4}-1,3-cyclobutadiene)$ -      78
Iron, $tricarbonyl(\eta^{4}-1,3-cyclohexadiene)$ -, coupling with alkenes      44
Iron, $tricarbonyl(\eta^{4}-1,3-cyclohexadiene)$ -, ox. coupling with carbon nucleophiles      44
Iron, anionic carbonyl complexes      see “Ferrate ...”
Isobutyryl chloride, $\alpha$ -acetoxy-      160
Isocyanates, blocking of OH with      301
Isocyanates, blocking of SH with      229 238
Isocyanates, synthesis      143 301 331
Isocyanides, trapping of diallylnickel      41
Isodrin, pagodane and dodecahedrane from      336—337
Isodrin, pr.      192
Isoephedrine, $(\pm)$ -      302
Isomerization, configurational, $E\rightarrow Z$ and/or $Z\rightarrow E$ of alkenes via 1,2-diol thiocarbonates      142
Isomerization, configurational, $E\rightarrow Z$ and/or $Z\rightarrow E$ of alkenes with hydrogenation catalyst      100—102
Isomerization, configurational, $E\rightarrow Z$ and/or $Z\rightarrow E$ of alkenes, photochemical      31 282 296 332
Isomerization, configurational, $E\rightarrow Z$ and/or $Z\rightarrow E$ of alkenes, thermal or iodine-catalysed      31
Isomerization, configurational, cis/trans or $\alpha/\beta$ at rings      see “Epimerization”
Isomerization, constitutional      see “Rearrangements”
Isopinocampheyl, chiral auxiliary group      108
Isoprene      see “1 2-methyl-”
Isopropamide iodide, $(\pm)$ -      302
Isoquinolines      292—293
Isoquinuclidine derivs. = 2-azabicyclo[2.2.2]-octane derivs., retro-synthesis      212—213
Isoquinuclidine derivs. = 2-azabicyclo[2.2.2]-octane derivs., synthesis      153 291 297
Isothioureas, S-alkyl-, thiols from      168
Isoureas, O-acyl- = carbamimidic anhydrides, reactive intermediates      144—145 234
Isoureas, O-alkyl- = carbamimidic esters      144—145
Isoxazoles      307—308
Isoxazoles, 4,5-dihydro-      153
Isoxazolidines      153
Jasmone = (Z)-3-methyl-2-(2-pentenyl)-2-cyclopenten-1-one      29
Jones’ reagent      see “Chromium(6+) oxide with sulfuric acid”
Juglone = 5-hydroxy-1,4-naphthalenedione, dienophilc in tetracycline synthesis      318
Julia — Lythgoe olefination      34
Julia’s terpenoid synthesis      69—70
Juvenile hormone, synth. steps      20 30 135 155
KAPA      see “1 mono-K
Katsuki — Sharpless oxn.      see “Sharpless epoxidation”
Kekulene = 15,23:16,22-dimethenobenzo[1,2-a:5,4-a']dipentaphene      338
Kemp’s acid      346—347
Kemp’s acid, molecular complexes of derivatives      346—348
Ketenes      see “Ethenone”
Ketimines      see “Imines”
Ketones, $\alpha$ -(alkylsulflnyl)-, synthesis and conversions      50—51 65
Ketones, $\alpha$ -acidity of      10
Ketones, $\alpha$ -activation of      see “Enamines” “Enolates” “Vinylogous
Ketones, $\alpha$ -acylation of      81
Ketones, $\alpha$ -acylation of, via enamines      88
Ketones, $\alpha$ -acylation of, via sulfur extrusion      59—60
Ketones, $\alpha$ -acylthic, S extrusion from      59—60
Ketones, $\alpha$ -alkoxy-, by oxn. of alkynes      117 132
Ketones, $\alpha$ -alkylation of      24—26 82 87
Ketones, $\alpha$ -amino-, pyrroles from      150—151
Ketones, $\alpha$ -amino-, synthesis from enol ethers      268
Ketones, $\alpha$ -amino-, synthesis from ketones      147 151 302
Ketones, $\alpha$ -halo-, $a^{2}$ -synthons      2 16 18
Ketones, $\alpha$ -halo-, $\alpha$ -alkylation with C nucleophiles      63
Ketones, $\alpha$ -halo-, $\alpha$ -amination      302
Ketones, $\alpha$ -halo-, Favorskii rearr. of      78 84
Ketones, $\alpha$ -halo-, reduction to oxiranes, enantioselective      108
Ketones, $\alpha$ -hydroxy- (acyloins), Birch type a-deoxygenation      156 277
Ketones, $\alpha$ -hydroxy- (acyloins), conversion to imidazoles      151—152
Ketones, $\alpha$ -hydroxy- (acyloins), synthesis of, by oxidation of alkynes      132
Ketones, $\alpha$ -hydroxy- (acyloins), synthesis of, by oxidation of ketones      116 121—122
Ketones, $\alpha$ -hydroxy- (acyloins), synthesis of, by redn. of 1,2-diones with $\mathrm{(RO)_{3}P}$       219
Ketones, $\alpha$ -hydroxy- (acyloins), synthesis of, from carbonyl compounds with 1,3-dithiane anions      51
Ketones, $\alpha$ -hydroxy- (acyloins), synthesis of, from carbonyl compounds with 1-alkyne anions      52
Ketones, $\alpha$ -hydroxy- (acyloins), synthesis of, from carboxylic acid esters by acyloin coupling      53—54
Ketones, $\alpha$ -hydroxy- (acyloins), synthesis of, from carboxylic acid esters with DMSO anion      51
Ketones, $\alpha,\beta$ -dehydrogenation of      138—140
Ketones, $\alpha,\beta$ -unsaturated, $\alpha$ - and $\alpha'$ -alkylation of      24—25 82 277
Ketones, $\alpha,\beta$ -unsaturated, $\alpha,\beta$ , p-dialkylation      277
Ketones, $\alpha,\beta$ -unsaturated, $\beta$ -alkylation of      20—21 277
Ketones, $\alpha,\beta$ -unsaturated, conversion to cyclobutanones      75/77
Ketones, $\alpha,\beta$ -unsaturated, conversion to cyclopentanones      75/77 83
Ketones, $\alpha,\beta$ -unsaturated, Favorskii rearr. of      84 211
Ketones, $\alpha,\beta$ -unsaturated, hydration of      274—275
Ketones, $\alpha,\beta$ -unsaturated, oxidative cleavage of      82
Ketones, $\alpha,\beta$ -unsaturated, reduction of, to alkenes      109
Ketones, $\alpha,\beta$ -unsaturated, reduction of, to allylic alcohols      105—107
Ketones, $\alpha,\beta$ -unsaturated, reduction of, to enolates with Li      73
Ketones, $\alpha,\beta$ -unsaturated, reduction of, to enolates with RMgBr      281
Ketones, $\alpha,\beta$ -unsaturated, reduction of, to ketones with $\mathrm{H_{2}}$ /catalyst      283
Ketones, $\alpha,\beta$ -unsaturated, reduction of, to ketones with Li      73 103—104
Ketones, $\alpha,\beta$ -unsaturated, synthesis of, by $\alpha,\beta$ -dehydrogenation of ketones      122 138—140
Ketones, $\alpha,\beta$ -unsaturated, synthesis of, by $\beta$ -eliminations      57 138 140 274
Ketones, $\alpha,\beta$ -unsaturated, synthesis of, by $\beta$ -eliminations of sulfoxides      65 86
Ketones, $\alpha,\beta$ -unsaturated, synthesis of, by aldol type condensations      59 71—73 81 82 280
Ketones, $\alpha,\beta$ -unsaturated, synthesis of, by Horner oleflnation      29
Ketones, $\alpha,\beta$ -unsaturated, synthesis of, by Mannich reactions      57
Ketones, $\alpha,\beta$ -unsaturated, synthesis of, by oxidation of allylic $\mathrm{CH_{2}}$       116 119—120
Ketones, $\alpha,\beta$ -unsaturated, synthesis of, by oxidation of allylic alcohols      118 133—135 323
Ketones, $\alpha,\beta$ -unsaturated, synthesis of, by reduction of alkoxyarenes      278
Ketones, $\beta$ -amino- (Mannich bases), $\beta$ -elimination of      57 72—73
Ketones, $\beta$ -amino- (Mannich bases), pr.      178
Ketones, $\beta$ -amino- (Mannich bases), synthesis      57 300 304
Ketones, $\beta$ -hydroxy-, synthesis by aldol type addn      55—58 60—62
Ketones, $\beta$ -hydroxy-, synthesis by hydration of 2-enones      274—275
Ketones, $\gamma,\delta$ -unsaturated, synth. by Torgov reaction      71 278—279
Ketones, (triphenylphosphoranylidene)hydrazones, Barton olefination of thiones with      35
Ketones, 1,2-oxygen shift procedure      156
Ketones, 1-alkenylation of      62—63
Ketones, 1-alkylation of      44
Ketones, 1-alkynylation of      52 62—63 278
Ketones, 1-allylation of      66—69
Ketones, conversion of, to $\alpha$ -chloro aldehydes ( $\mathrm{LiCHCl_{2}}$ )      51—52
Ketones, conversion of, to $\alpha$ -hydroxy aldehydes (TosMIC)      49 51
Ketones, conversion of, to aldehydes ( $\mathrm{Ph_{3}P=CH-OR}$ )      48—49
Ketones, conversion of, to cyclopropanol silyl ethers      75 83
Ketones, conversion of, to enamines      13 88
Ketones, conversion of, to enol silyl ethers      11 58 75 83
Ketones, conversion of, to enolates      11—12 24—25 58
Ketones, conversion of, to nitriles (TosMIC)      49
Ketones, conversion of, to oxiranes (sulfonium ylides)      28 45
Ketones, cyclic, 5-membered, synthesis      81—83
Ketones, cyclic, selective monoalkylation      25—26
Ketones, cyclic, synthesis, Birch redn. of alkoxyarenes      103—104 278
Ketones, cyclic, synthesis, from dienes and $\mathrm{RBH_{2}/CO}$       47—48
Ketones, homologization of, by diazoalkanes      83 166
Ketones, olefination      28—35 41 110 267
Ketones, oxidative a-coupling via enol ethers      65
Ketones, oxidative cleavage of, Beckmann rearr. to lactams      136—137
Ketones, oxidative cleavage of, by $\mathrm{CrO_{3}}$ via enol ethers      285
Ketones, oxidative cleavage of, by $\mathrm{H_{2}O_{2}}$ via $\alpha$ -(arylmethylene) ketones      82
Ketones, oxidative cleavage of, by $\mathrm{KMnO_{4}}$       137
Ketones, oxidative cleavage of, by fragmentation via a-dithioketals      79
Ketones, oxidative cleavage of, to esters or lactones      80 136 165 206 210 276 282 283 319—320
Ketones, protection of      see “Protection of carbonyl groups”
Ketones, rearrangements via tosylhydrazones      141—142
Ketones, reduction of, to alcohols      98 105—108
Ketones, reduction of, to alcohols, enantiosel      102—103 108 325—326
Ketones, reduction of, to alkanes      98 109
Ketones, reduction of, to alkenes      141—142
Ketones, reduction of, to amines via imines or oximes      98 112

Ketones, reductive coupling of      35 41 53
Ketones, reductive coupling of, with 2-enoic esters      69
Ketones, synthesis of, form aldehydes via 1,3-dithianes      22 51
Ketones, synthesis of, form aldehydes via dicyanomethylene derivs.      166
Ketones, synthesis of, form alkenes via boranes + CO      47—48
Ketones, synthesis of, form alkenes, ox. cleavage      87—88 156—157 280 282
Ketones, synthesis of, form alkenes, ox. rearr. with $\mathrm{Tl^{3+}}$       129—130
Ketones, synthesis of, from 5(4H)-oxazolones + 2RX      48
Ketones, synthesis of, from arf-nitroalkanes, aq. acid      16 65—66
Ketones, synthesis of, from carboxylic acid derivs., $\mathrm{RX+Na_{2}Fe(CO)_{4}}$       46—47
Ketones, synthesis of, from carboxylic acid derivs., halides, $\mathrm{R_{2}CuLi}$ or RZnX      45—46
Ketones, synthesis of, from carboxylic acid derivs., lithium salts, RLi      45—46 282
Ketones, synthesis of, from carboxylic acid derivs., nitriles, RMgX      201 298—299
Ketones, synthesis of, from carboxylic acid derivs., thioesters, RLi or RMgX      319—320
Ketones, synthesis of, from diallylic Ni complexes + RNC      41
Ketones, synthesis of, from dithioacetals + RX      22 51 66 205
Ketones, synthesis of, from enol or enamine derivatives, hydrolysis      48—49 103—104 278
Ketones, synthesis of, from enol or enamine derivatives, ox. cleavage with $\mathrm{CrO_{3}}$ or $\mathrm{O_{3}}$       280 285
Ketones, synthesis of, from hydrazones, $\mathrm{O_{3}}$       26
Ketones, synthesis of, from nitroalkenes, reduction      301
Ketones, synthesis of, from sec. alcohols by oxidation      133—135 267 276—277 283 322—323 328—329 337
Ketones, synthesis of, from tetracarbonylferrate(2-)/CO      46—47
Ketones, synthesis of, from thioenol ethers by hydrolysis      83
Kinetic control, diastereotoposelective lactonization      168
Kinetic control, directed aldol addns.      56—62
Kinetic control, enolate formation      11—13 24—25 58
Kinetic control, Wittig olefination      28—31
Kinetic protonation of enolates      322—323
Kinetic resolution      see “Optical resolution”
Knoevenagel condensation      56 58—59 166
Knorr’s pyrrole synthesis      150—151
Koenigs — Knorr glycosylation with glycosyl halides and mercury(2+)      267
L-Arabinitol, 1,2:4,5-dianhydro-, prepn.      160 327—328
L-Arabinitol, chiral educt      160 327—328
L-Arginine, pr.      184
L-Arginine, protection      229
L-Cysteine, cephalosporin from      313—314
L-Cysteine, pr.      185
L-Cysteine, S-protection      229
L-Glutamic acid, chiral educt      202—203
L-Glutamic acid, pr.      184
L-Glutamic acid, protection      229
L-Hexoses, total synthesis      264—265
L-Homoproline, FK 506 synthon      324 326—327
L-Mandelic acid = (S)-hydroxyphenylacetic acid, chiral auxiliary from      62
L-Proline, chiral ligand from      20—21
L-Proline, N,O-protection      299
L-Proline, stereoselectivity $\alpha$ -alkylation      299
L-Serine, $\beta$ -lactams from serine amides      161
L-Serine, educt for chiral auxiliary      23
L-Serine, pr.      184
L-Serine, protection      229
L-Streptose, synthesis      267
L-Valinol = (S)-2-amino-3-methyl-butanol, chiral auxiliary      61
Lactams, macrocyclic, synthesis      240—241 247 249—250 328—329
Lactams, pr.      178 184
Lactams, synth. from cyclic ketoximes      136—137 195
Lactones, $\alpha$ -alkylation, diastereoselective      321 322 327—328
Lactones, macrocyclic, synthesis by intramol. allyl coupling      42
Lactones, macrocyclic, synthesis by intramol. esterification      145—146
Lactones, reduction to cyclic ethers      110—111
Lactones, reduction to cyclic hemiacetals      105 321 322 327—328
Lactones, synthesis by Baeyer — Villiger oxidation      80 136 165 206 210 276 319—320
Lactones, synthesis by halolactonization      275 319—320 321
Lactones, synthesis by intramol. esterification      63—65 69 70 145—146 168 273 322 325 327—328
Ladenburg benzene = prismane      330—331
Lanosta-8,24-dien-3-ol, $(3\beta)$ - (lanosterol), biosynthesis, syntheses relating to      279—280
Lanosta-8,24-dien-3-ol, $(3\beta)$ - (lanosterol), pr.      284
Lawesson type reagents      110—111
LDA      see “2-Propaneamine N-(1-methylethyl)- lithium
Lead(2+) acetate, additive for Lindlar cat      100
Lead(2+) acetate, basic acetate, $\mathrm{Pb_{2}(OAc)_{3}OH}$ , catalyst for aldol type condensation      318
Lead(4+) acetate, oxidation with, of alcohols to aldehydes      117 133
Lead(4+) acetate, oxidation with, of amines to nitrenes      212—213
Lead(4+) acetate, oxidation with, of hydrazines to diazenes      35
Lead(4+) acetate, oxidative degradation of 1,2-dicarboxylic acids      80 142 333
Lead(4+) acetate, oxidative degradation of a-amino acids      48
Lead(4+) acetate, oxidative degradation of carboxylic acids with $\mathrm{I_{2}}(h\cdot\nu)$       337
Lecithins, vesicle membranes      350
Leukotriene $\mathrm{B_{4}}$ , synthesis      125—126
Lewis acids      see “Aluminum(3+) chloride” “Borane trifluoro-” “Lithium(1+)” “Magnesium(2+)” “Mercury(2+)” “Silvei(1+)” “Thallium(1+)” “Tin(4+) “Titanium(4+) “Zinc(2+)”
Librium      307
Ligands, macrocyclic      235—237 241 247—262
Lindlar catalyst      100
Lindlar catalyst, hydrogenation of alkynes      40 64 100—101
Linear synthesis vs. convergent synthesis, disadvantages      224—225 233—234
Lipase, pig pancreatic      167
Lipid membranes      350—351
Lithium(1+), complex or organic salts (except organyls)      see corresponding acid or anion
Lithium(1+), perchlorate, cat. for Diels — Alder addition      86
Lithium(1+), salts, cat. for dehydrogenation      52 140
Lithium(1+), salts, cat. for rearr. of oxiranes      52 77 79
Lithium, (1,1-dimethylethyl)- ( $\mathrm{Bu^{t}Li}$ ), halogen-metal exchange with      70 326—327
Lithium, (1,1-dimethylethyl)- ( $\mathrm{Bu^{t}Li}$ ), lithiation with, of sulfones      8
Lithium, (1,1-dimethylethyl)- ( $\mathrm{Bu^{t}Li}$ ), lithiation with, of thioesters      323
Lithium, (1,1-dimethylethyl)- ( $\mathrm{Bu^{t}Li}$ ), prepn. of $\mathrm{Bu^{t}Me_{2}SiSLi}$ from      169
Lithium, (1,3-dithian-2-yl)-      see “1
Lithium, (1-methylpropyl)- ( $\mathrm{Bu^{s}Li}$ ), lithiation of allylic CH groups      14 15
Lithium, (2-methoxycyclopropyl)-, cis-, $d^{3}$ -synthon      14—15 19 70 76
Lithium, (2-methoxycyclopropyl)-, cis-, prepn.      70
Lithium, (ethoxyethynyl)-, carboxymethyl $d^{2}$ -synthon      64—65 325 327—328
Lithium, (triphenylmethyl)- (trityllithium, $\mathrm{Ph_{3}CLi}$ ), selective enolization with      11—12
Lithium, alkyl-, addn. to 1-aikenyl silanes      34
Lithium, alkyl-, addn. to lithium carboxylates      45—46 283
Lithium, alkyl-, addn. to thionolactones      110—111
Lithium, butyl- (BuLi)      5
Lithium, butyl- (BuLi), lithiation with, of 1-alkynes      64—65 303 325 328
Lithium, butyl- (BuLi), lithiation with, of 1-alkynes, 1,3-dilithiation      281
Lithium, butyl- (BuLi), lithiation with, of allylic and benzylic CH groups      10 14
Lithium, butyl- (BuLi), lithiation with, of carboxylic acids (dilithiation)      63
Lithium, butyl- (BuLi), lithiation with, of dithioacetals      6 8 22 51 66
Lithium, butyl- (BuLi), lithiation with, of imidic esters      22—23
Lithium, butyl- (BuLi), lithiation with, of phosphonic diamides      328 329
Lithium, butyl- (BuLi), lithiation with, of phosphonium salts      6 31—32
Lithium, butyl- (BuLi), lithiation with, of sec. carboxamides      61
Lithium, butyl- (BuLi), lithiation with, of silanes (activated)      7
Lithium, butyl- (BuLi), lithiation with, of sulfones      34
Lithium, butyl- (BuLi), lithiation with, of sulfonium salts      45 154
Lithium, butyl- (BuLi), lithiation with, of tosylhydrazones      141
Lithium, dichloromethyl, addn. to ketones      51—52
Lithium, ethenyl- (vinyllithium)      5
Lithium, ethynyl-, addition to oxiranes      321
Lithium, metalation of organyl halides with      5—6
Lithium, methyl-, alkyl d-synthon      1—2 79 283
Lithium, methyl-, cleavage of silyl enolates with      57—58 73
Lithium, methyl-, halogen-metal exchange with      74—75
Lithium, methyl-, lithiation with, of sulfoxides      9
Lithium, methyl-, lithiation with, of tosylhydrazones      141
Lithium, methyl-, metal-metal exchange, with Cu(1+)      5 20
Lithium, methyl-, transmetalation of organylstannanes      322—323
Lithium, reduction with      see “Birch reduction”
Lithium, reductive desulfurization of sulfones      70
Lithium, [(methylthioXtrimethylsilyl)methyl]-, Peterson olefination with      34
Lithium-biphenyl reagent, 10-demethylation of steroids      287—288
Lithium-naphthalene reagent, deprotonation of 1-alkynes      52
Lysine, pr.      184
Lysine, protection      229 241
Macrocycles      see “Carbocycles macrocyclic”
Macrocycles, lactams      247 249—250 324—329
Macrocycles, lactones      42 145—146 319—329
Macrocycles, ligands      235—236 247 249—250
Macrocycles, peptides      235—236 241
Macrocycles, peptides, solid-phase method      241
Macrolides      see “Lactones macrocyclic”
Magnesium(2+) halides, catalysts, for allylstannane addn. to RR'CO      66—67
Magnesium(2+) halides, catalysts, for cyclopropanemethanol opening      70 77
Magnesium(2+) halides, transmetalation of organyllithium      326—327
Magnesium, alkylhalo-, metal-metal exchange of      5 7 20 46
Magnesium, alkylhalo-, preparation      7 20 46 326—327
Magnesium, bromoethenyl-, ethenylation with      18 62—63

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