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

Phosphorous triamide, hexamethyl-, Mitsunobu type reactions with      161
Phosphorous tribromide, OH/Br exchange      303
Phosphorous trichloride, glycosyl halides      266
Phosphorus(5+) chloride, amide cleavage with      311—313
Phosphorus(5+) chloride, prepn. of acid halides with      143
Phosphorus(5+) oxide ( $\mathrm{P_{4}O_{10}}$ ), Bischler — Napieralski isoquinoline synth.      293
Phosphoryl chloride (phosphorus oxychloride), Vilsmeier reagents from      16 —255 293
Photochemical reactions, $6\pi$ -electrocyclizations      295—296 338
Photochemical reactions, 1,3-cyclohexadiene opening      289
Photochemical reactions, decomposition of $\alpha$ -diazo ketones      337
Photochemical reactions, decomposition of acyl hypoiodites      337
Photochemical reactions, decomposition of azides      154
Photochemical reactions, E/Z isomerizn. of alkenes      31 282 296 332
Photochemical reactions, elimination of 1,2-dicarboperoxoic esters      142
Photochemical reactions, extrusion of $\mathrm{N_{2}}$       334
Photochemical reactions, extrusion of CO      330 339
Photochemical reactions, extrusion of sulfur (with $\mathrm{P^{III}}$ )      39
Photochemical reactions, oxidation of alkyl groups      116 285—286
Photochemical reactions, skeletal rearr. of strained polycycles      329—333
Photochemical reactions, [2+2]cycloaddition, alkene + alkene      78 297—298 330 333
Photochemical reactions, [2+2]cycloaddition, alkene + oxygen (ox. cleavage)      259
Photochemical reactions, [2+2]cycloaddition, benzene + benzene      336—337
Photochemical reactions, [2+2]cycloreversion      333
Photochemical reactions, [2+4]cycloaddition, photooxygenation, diene + oxygen      102 276—277
Photosynthetic reaction centre, models      348—350
Phthaloyl protecting group      163 315
Picted — Spengler cyclization      292
Pig pancreatic lipase      167
Pinacol coupling      53
Pinacolone rearrangement of 1,2-diol monotosylate      32
Pinane derivs., pr.      192
Pincer Diels — Alder addition      335—336
Piperazine, asymm. 1,4-dialkylation      304
Piperazine, industrial synthesis      149
Piperazine-2,5-diones (diketopiperazines)- by products in peptide synthesis      237
Piperidine derivs., synthesis      304
Piperidine, enamines from      13—14
Piperidine-2,6-diones, synthesis      304
Piperidinium acetate, cat. for aldol addn      82
Pivalaldehyde, amino acid N,O-protection      299
Pivampicillin      312
Pixyl protecting group      341—342
Plasmids, vehicles for gene transfer      242—246
Platinum, hydrogenation catalyst      105 109 113
Platinum, rearrangement of carbon cages with      336
Platyphyllide, retro-synthesis      208
PMB (p-methoxybenzyl) ethers      157 326—329
Polycyclic carbon skeletons, syntheses      3 90—94 208—212 329—339 356—357
Polymerase chain reaction      226—227
Polymeric supports      see “Solid-phase synthesis”
Polystyrene derivs.      see “Benzene ethenyl- homopolymer”
Porphobilinogen, cyclotetramerization      251—252
Porphodimethenes      255
Porphyrin oligomers, arylene-linked, stacked, stretchei and tilted      348—350
Porphyrin, “capped”      253
Porphyrin, “picked-fence”      253
Porphyrinogens      250—252
Porphyrins      250—257
Porphyrins, 5,10,15,20-tetrasubstituted      252—253
Porphyrins, assemblies, covalent/non-covalent      348—350
Porphyrins, micellar fibers (amphiphilic porphyrins)      350
Porphyrins, natural, total synthesis      251—252 255—257
Porphyrins, numbering      252
Porphyrins, reduction of      251 258—259
Porphyrins, unsymmetrical      256—257
Porphyrins, water-soluble      252
Potassium(1+), complex or organic salts (except organyls)      see corresponding acid or anion
Potassium, (triphenylmethyl)- ( $\mathrm{Ph_{3}C^{-}K^{+}}$ ), enolate formation with      58
Potassium, preparation of Ti(0) with      41
PPY      see “Pyridine 4-(1-pyrrolidinyl)-”
Pregn-4-ene-3,20-dione (progesterone), $(\pm)$ -, total synthesis      279—280
Pregn-4-ene-3,20-dione (progesterone), pr.      284
Previtamin $\mathrm{D_{2}}$       289
Previtamin $\mathrm{D_{3}}$ , $1\alpha$ -hydroxy-, synthesis      34
Prevost glycolization      127
prim. Amines, addn. of to 2-enones      291
prim. Amines, addn. of to 2-enones to oxiranes      291
prim. Amines, conversion to alcohols      202—203
prim. Amines, oxidation to nitrenes, $\mathrm{Pb(OAc)_{4}}$       212—213
prim. Amines, synthesis by degradn. of carboxylic acid derivs.      139 143 301 308 331
prim. Amines, synthesis by reduction of azides      267
prim. Amines, synthesis by reduction of nitriles      50 98
prim. Amines, synthesis by reduction of nitroalkanes      60 98 112 253 297
prim. Amines, synthesis by reduction of nitrosoalkanes      268
prim. Amines, synthesis from alcohols      267
Primers for DNA synthesis by PCR      226—227
Primers, mismatch-, for single-site mutation      245—246
Prismane = $tetracyclo[2.2.0.0^{2,6}.0^{3,5}]hexane$ (Ladenburg benzene)      330—331
Prochirality, terminology      167 359—360
Prochlorperazine      310
Promethazine, $(\pm)$ -      310
Propadrine, $(\pm)$ -      302
Propanal, 2,2-dimethyl- (pivalaldehyde), N,O-protection of proline      299
Propane, 1,3-dibromo-, alkylation with      23
Propane, 1-bromo-3-chloro-, drug synthesis with      304 310
Propane, 1-bromo-3-chloro-, pr.      180
Propane, 2-isocyano-2-methyl- ( $\mathrm{Bu^{t}NC}$ ), diallylnickel trapping with      41
Propanedinitrile, carbon acidity      10
Propanedinitrile, protecting reagent      166
Propanedioic acids, esters, alkylation      23 44 199—200
Propanedioic acids, esters, allylation with $\pi$ -allylpalladium complexes      27
Propanedioic acids, esters, carbon acidity      10
Propanedioic acids, esters, carboxymethyl $d^{2}$ -synthon      19 139 199—200
Propanedioic acids, esters, drugs from      302 305—306
Propanedioic acids, esters, Knoevenagel condensation with      56
Propanedioic acids, esters, Michael addition with      72
Propanedioic acids, esters, pr.      177
Propanenitrile, 2,2'-azobis[2-methyl- (AIBN, $\alpha,\alpha'$ -azoisobutyronitrile), radical initiator      111
Propanenitrile, 2-hydroxy-2-methyl- (acetone cyanohydrin), educt      201
Propanenitrile, 2-hydroxy-2-methyl- (acetone cyanohydrin), pr.      176
Propanenitrile, 3-hydroxy-, phosphate protection, 2-cyanoethyl (Ce) esters      166—167 216 218 220—221 224
Propanenitrile, 3-hydroxy-, pr.      176
Propanoic acid, 2-bromo-, ethyl ester, pr.      179
Propanoic acid, 2-bromo-, ethyl ester, Reformatsky reaction with      44—45
Propanoyl chloride, 2-(acetyloxy)-2-methyl- (Moffatt’s reagent)-, chlorohydrins from diols      160 327—328
Propanoyl chloride, 2-(acetyloxy)-2-methyl- (Moffatt’s reagent)-, O-protection      160
Propionic acid      see “Propanoic acid”
Prostaglandins      273—277
Prostaglandins, cyclopentane precursor      159 210 275—277
Prostaglandins, partial synthesis      274—275
Prostaglandins, total syntheses      275—277
Protection      154—167 (see also “Capping” “Deblocking”)
Protection of $\alpha$ -methylene groups of acetoacetic esters, deprotonation      9 24 204 326
Protection of $\alpha$ -methylene groups of ketone, arylmethylene derivatives      82
Protection of $\alpha$ -methylene groups of ketone, butylthiomethylene derivatives      155—156
Protection of $\alpha$ -methylene groups of ketone, thioketals      79 155—156
Protection of 1-alkynes, deprotonation      100—101
Protection of 1-alkynes, silylation      155 339
Protection of amino acids, N,O-alkylidene derivs.      299
Protection of amino groups, amides and carbamates      161—164 216 220—221 228—229 304 327 342
Protection of amino groups, complexation with metal ions      293—294
Protection of amino groups, oxazolones (“Ox” derivs.)      161 164
Protection of amino groups, phthalimides      163
Protection of amino groups, quaternization      293 304
Protection of amino groups, sulfonamides      247 304
Protection of carbon-carbon double bonds, 1,2-dihalides      119 156—157
Protection of carbon-carbon double bonds, oxiranes      156—157
Protection of carbonyl groups, acetals      18 20 24 49 75 104 106 122 135 165—166 279 291 298 337 339 349
Protection of carbonyl groups, dicyanomethylene derivatives      166
Protection of carbonyl groups, dithioacetals      76 165—166
Protection of carbonyl groups, monothioacetals      76 165—166
Protection of carbonyl groups, olefination      321—323
Protection of carboxy groups, 2,2,2-trihaloethyl esters      165
Protection of carboxy groups, esters      32 37 47—48 165 229 307
Protection of carboxy groups, silyl esters      313
Protection of diols, cyclic acetals      158 209—210 263—269 271 272 276—277 318 321—323 326
Protection of enols, (1,1-dimethylethyl)dimethylsilyl ethers      325
Protection of enols, acetic esters      58 318
Protection of enols, dialkylborinic esters      12—13 60—62
Protection of enols, ethers      48—49 103—104 278

Protection of enols, trimethylsilyl ethers      11 53—54 57—58 73 75 83 86 209—210 281
Protection of guanidino groups      229
Protection of hydroxy groups      157—161 (see also “Monosaccharides” “Nucleotides”)
Protection of hydroxy groups, carbonic and carboxylic esters      55 75 157—158 160—161 216 266—273 276—277 282 283
Protection of hydroxy groups, ethers, (1,1-dimethylethyl)dimethylsilyl (Tbdms, Tbs, $\mathrm{SiBu^{t}Me_{2}}$ )      34 65 67 69 131 157 159 160 276—277 281—282 320—325 327—329
Protection of hydroxy groups, ethers, (1,1-dimethylethyl)diphenylsilyl      110 272
Protection of hydroxy groups, ethers, (4-methoxyphenyl)methyl (MPM, PMB)      157 270 325—329
Protection of hydroxy groups, ethers, 1,1-dimethylethyl (tert-butyl, $\mathrm{Bu^{t}}$ )      229 280 283
Protection of hydroxy groups, ethers, 2,4,4-trimethyl-5-oxo-1,3-dioxolan-2-yl (Moffat dioxolanone)      160
Protection of hydroxy groups, ethers, 2-propenyl (allyl)      270
Protection of hydroxy groups, ethers, 9-phenyl-9H-xanthen-9-yl (pixyl, Px)      341—342
Protection of hydroxy groups, ethers, diphenylmethyl (benzhydryl, $\mathrm{Ph_{2}CH}$ )      265
Protection of hydroxy groups, ethers, methoxymethyl (MOM)      84 318
Protection of hydroxy groups, ethers, methyl, irreversible      23 157 161 272
Protection of hydroxy groups, ethers, methyl, reversible      280
Protection of hydroxy groups, ethers, phenylmethyl (benzyl, Bzl, Bn, $\mathrm{PhCH_{2}}$ )      131 157—159 161 229 241 270—272 301 305 328—329
Protection of hydroxy groups, ethers, tetrahydro-2ff-pyran-2-yl (Thp)      26 82 157 159—160 201 216 273
Protection of hydroxy groups, ethers, triethylsilyl ( $\mathrm{SiEt_{3}}$ )      328—329
Protection of hydroxy groups, ethers, trimethylsilyl ( $\mathrm{SiMe_{3}}$ , Tms)      14 15 70 75 83 159 275 281—283 315
Protection of hydroxy groups, ethers, triphenylmethyl (trityl, Tr), p-methoxytrityl (Mtr), di—p—methoxytrityl (Dmtr)      159—160 216 218—224 343
Protection of hydroxy groups, ethers, tris(1-methylethyl)silyl ( $\mathrm{SiPr^{i}_{3}}$ )      324—329
Protection of hydroxy groups, iodoetheriflcation      272 326—327
Protection of hydroxy groups, lactones      319—320 321—322 327—328
Protection of mercapto groups      169 229 237—240
Protection of nucleic acid sequences      344
Protection of phenols, methyl ethers      280
Protection of phenols, phenylmethyl (benzyl) ethers      301 305
Protection of phosphate groups      166—167 216—224
Protection of phosphate groups, 1-methyl-2-oxopropyl (acetoinyl, Acn)      219
Protection of phosphate groups, 2,2,2-trichloroethyl (Tce)      167 216 220
Protection of phosphate groups, 2-cyanoethyl (Ce)      166—167 216 220—224
Protection of phosphate groups, 2-[[4-(triphenylmethyl)phenyl]thio]ethyl (Tpte)      216 217
Protection of phosphate groups, 4-chlorophenyl      218
Protection of phosphate groups, methyl (Me)      220—224
Protection of thioether groups, sulfoxides      229
Pseudodiosgenin      285
Pseudoephedrine, $(\pm)$ -      302
Pseudoionone, cyclization      90—91
PTC = phase-transfer catalysts      see “Benzene methanaminium” “Butamiminium” “18-Crown-6”
Pulegone      see “Cyclohexanone 5-methyl-2-(1-methylethylidene)-”
Pummerer rearrangements      51 265
Px, pixyl protecting group      341—342
Pyrene, 10b,10c-dihydro-10b,10c-dimethyl-, trans-      38
Pyridine, 2,6-bis(1,1-dimethylethyl)-, bulky base      321
Pyridine, 2,6-bis(1,1-dimethylethyl)-, hydrochloride, kinetic protonation with      323
Pyridine, 2,6-dimethyl-, bulky base      223 322 329
Pyridine, 4-(1-pyrrolidinyl)- (PPY), acylation catalyst      145 326—327
Pyridine, attenuation of $\mathrm{O_{3}}$ -reactivity      326
Pyridines, 2-halo-, 2-alkylation      303—304
Pyridines, redn.      112—113 212 297 303 309
Pyridinium ions, nucleophilic alkylation      309
Pyridinium ions, reduction      112—113 212 297
Pyridinium, 2-chloro-1-methyl-, iodide (Mukaiyama’s macrolactamization agent)      328—329
Pyridinium, chlorochromate      see “Chromate(1-)”
Pyrrolidine, 2-(methoxymethyl)- (S)-, chiral ligand      20—21
Pyrrolidine, enamines from      13—14
Pyrrolo[1,2-a]pyrimidine, 2,3,4,6,7,8-hexahydro- (1,5-diazabicyclo[4.3.0]non-5-ene, DBN), HBr elimination with      334
Pyrromethanes      see “Dipyrromethanes”
Pyrromethenes      see “Dipyrromethenes”
Quaternary ammonium      see “Ammonium”
quaternary Ammonium compounds, Hofmann elimination      72 140—141 331
quaternary Ammonium compounds, phase-transfer catalysts      see “Benzenemethanaminium” “1-Butanaminium”
quaternary Ammonium compounds, thermal demethylation      304
Quinidine, 10,11-dihydro-, chiral $\mathrm{OsO_{4}}$ -catalyst      129
Quinidine, pr.      290
Quinine, 10,11-dihydro-, chiral $\mathrm{OsO_{4}}$ -catalyst      129
Quinine, pr.      290
Quinoiines, synthesis by Heck coupling      43
Quinones      see “Cyclohexadienediones”
Quinuclidine derivs. = 1-azabicyclo[2.2.2]octanes, drug synthesis      309
Quinuclidine derivs. = 1-azabicyclo[2.2.2]octanes, pr.      290
Racemates, resolution of      see “Optical resolution”
Racemization, prevention in $\beta$ -lactam formation      161
Racemization, prevention in peptide synthesis      145 231—232 234
Radical synthons, $r^{1}$ , ketyl radical anions      53—54
Radical synthons, $r^{2}$ , enol radicals      65
Radical synthons, $r^{3}$ , allyl radicals      41—42 84
Radical synthons, alkyl r      20 35 36
Radical synthons, alkynyl $r^{2}$       40
Radicals in autoxidation of enolates      121
Radicals in oxidation of alkyl groups      286
Radicals in photoisomerizations      331—333
Radicals in reduction with tin hydrides      110—111
Raney $nickel^{\circledR}$ (activated Ni-Al alloy), catalytic hydrogenation of arenes      87
Raney $nickel^{\circledR}$ (activated Ni-Al alloy), catalytic hydrogenation of nitroalkenes      66 112
Raney $nickel^{\circledR}$ (activated Ni-Al alloy), cleavage of 1,3-oxathiolanes      165—166
Raney $nickel^{\circledR}$ (activated Ni-Al alloy), reductive desulfurization of sulfones      70
Raney $nickel^{\circledR}$ (activated Ni-Al alloy), reductive desulfurization of thioethers, thiols and dithioacetals      76 82 98 109 156 273
Rearrangement, retro-synthetic      195
Rearrangements      see “Ring contraction” “Ring “Ring
Rearrangements via carbenes      75 92 141—142
Rearrangements, acid-base-catalysed, of alkenes ( $\mathrm{H^{+}}$ shift)      85 90—91 101 274 278
Rearrangements, acid-base-catalysed, of O-acyl isoureas      144 234
Rearrangements, base-induced, of tosylhydrazones      141—142
Rearrangements, base-induced, of triorganylborane adducts      9 37—38
Rearrangements, cationic      see “Rearrangements oxidative”
Rearrangements, cationic, of $\alpha$ -(methylsulFinyl) ketones (Pummerer rearr.)      51 265
Rearrangements, cationic, of $\beta$ -chloro thioethers      314
Rearrangements, cationic, of 1,2-diols (pinacolone rearr.)      32
Rearrangements, cationic, of 2,5-cyclohexadien-1-ones      139
Rearrangements, cationic, of glycosides with 2-OH by $\mathrm{Et_{2}NSF_{3}}$       272
Rearrangements, cationic, of ketones etc. with $\mathrm{CH_{2}N_{2}}$       83 166
Rearrangements, cationic, of N-halo amines (Stieglitz rearr.)      77—78
Rearrangements, cationic, of oxiranes      52 77 79
Rearrangements, cationic, of porphyrinogens and dipyrromethanes      251—252 254
Rearrangements, metal-catalysed, of alkenes, H shift      90 101 270
Rearrangements, metal-catalysed, of allyl alcohols to aldehydes      43
Rearrangements, metal-catalysed, of oligocycloalkanes      79—80 332—333 336
Rearrangements, oxidative, of 1-alkenyl boranes      37—38
Rearrangements, oxidative, of 1-amino alcohols      76—77
Rearrangements, oxidative, of alkenes to carbonyl compds      129—130
Rearrangements, oxidative, of carbonyl compounds by peroxy acids      see “Baeyer — Villiger rearrangement”
Rearrangements, oxidative, of ketones by thallium(3+)      136
Rearrangements, oxidative, of oximes to amides (Beckmann rearr.)      136—137
Rearrangements, reductive, of diallylic disulfides      39
Rearrangements, sigmatropic      see “Pericyclic reactions”
Rearrangements, sigmatropic, [1,16]-, H shift in corrin synthesis      262
Rearrangements, sigmatropic, [1,2]-, of sulfonium ylides (Stevens rearr.)      38 338
Rearrangements, sigmatropic, [1,3]-, of (1-alkenyl)cyclopropanes      77 83
Rearrangements, sigmatropic, [1,3]-, of cyclopropanemethanimines      298—299
Rearrangements, sigmatropic, [1,5]-, H shift in alkaloid synthesis      295
Rearrangements, sigmatropic, [1,7]-, H shift of tachysterols      289
Rearrangements, sigmatropic, [2,3]-, in oxn. with $\mathrm{SeO_{2}}$       119 122
Rearrangements, sigmatropic, [2,3]-, of allylsulfonium ylides      39
Rearrangements, sigmatropic, [2,3]-, of diallyl thioethers with benzyne      39
Rearrangements, sigmatropic, [3,3]-, in Fischer’s indole synthesis      151—152
Rearrangements, sigmatropic, [3,3]-, of 6-allyl-2,4-cyclohexadien-1-ones      319—320
Rearrangements, transamidations, “zip” reaction      249—250
Recombinant DNA      241—246
Reduction      96—115 (see also corresponding compound classes “Birch “ reductive” “Hydrogenation”)
Reduction of $\alpha$ -(methylsulfinyl) ketones      51
Reduction of $\alpha$ -hydroxy ketones      156 277
Reduction of acid anhydrides or halides to aldehydes      46—47
Reduction of alkenes      96—97 101—104 130—131
Reduction of alkynes      64 96—97 100—102
Reduction of carbonyl compds      98 105—111 141—142
Reduction of carbonyl compds, enantioselective      108
Reduction of carboximidic esters to aldehydes      13 22—23 63—64 298
Reduction of carboximidic esters to sec. amines      111—112
Reduction of haloalkanes      97 113—115 202—203
Reduction of haloalkanes with chromium(2+)      286
Reduction of haloalkanes with hydrogen/Raney Ni      287
Reduction of haloalkanes with methyllithium      75
Reduction of haloalkanes with tributylstannane      97 114—115 275 319—320
Reduction of haloalkanes with zinc or zinc-copper      83 335—336
Reduction of hydroperoxides      121
Reduction of nitrogen compounds      111—113
Reduction of peroxides      277
Reduction, selectivity of reagents, tables      96—99
Reductive $\beta$ -climination      see “ $\beta$ -Elimination”

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