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

COD = Cod      see “1
Colchicine, synthesis step      146
Collins’ reagent      see “Chromium trioxobis(pyridine)-”
Collman’s reagent      see “Ferrate(2-) tetracarbonyl-”
Commercial chemicals, inexpensive tables      174—192 263—264 284 290
Complex hydrides      see “Aluminum” “Aluminate” “Borane” “Borate”
Configurational selectivity      see “Stereoselectivity”
Connection, retro-synthetic      195
Contraction of rings      see “Ring contraction”
Convergent growth of dendrimers      354—355
Convergent synthesis      224—225 239—240 280—281 324—329
Cope elimination of tert. amine N-oxides      140
Cope rearrangement of allylcyclohexadienone      319—320
Cope rearrangement, degenerate, of bullvalene      332—333
Cope rearrangement, degenerate, of semibulivalcne      331
Cope rearrangement, oxa- = Claisen rearrangement      87 325
Copper(1+) helicate complexes      345—346
Copper(1+) oxide ( $\mathrm{Cu_{2}O}$ ), oxidative 1,2-bis-decarboxylation      337
Copper(1+)/Copper(2+), 1-alkyne coupling with      40 154—155 339
Copper(1+)/Copper(2+), 1-alkynylation of iminium ions with      57
Copper(1-), diorganyl-      see “Cuprates(1-)”
Copper(2+), catalyst for oxn. of alkenes to diols with aq. $\mathrm{I_{2}/AcOH}$       128
Copper(2+), oxn. of $\alpha$ -hydroxy carbonyl compounds      133
Copper(2+), oxn. of alkenes to $\pi$ -allyl Pd complexes      27
Copper(2+), oxn. of hydrazines to diazenes      331
Copper, (1-alkynyl)-, 1-alkynyl d-synthon      339
Copper, (trimethylstannyl)-, $\mathrm{CuSnMe_{3}\cdot Me_{2}S}$ reagent, hydrostannylation of alkynes      321
Copper, organylbis(tributylphosphine)-, d-synthon      277
Copper/Copper(1+), catalyst for the generation of carbenes      74—75 94
Coproporphyria      256
Copy DNA (cDNA)      242
Corannulene = dibenzo[ghi,mno]fluoranthene      140
Corrins      259—262
Corrins, A/D-bipyrrolidine synthon      66 260
Corrins, methine bridges by S extrusion      59—60 261
Corroles      259
Corroles, reduction of      259
Corticrocin      40
Cortisol, $9\alpha$ -fluoro-      287
Coupling      see “Oxidative coupling” “Nucleotides” “Peptides” “Reductive
Coupling, Pd(0)-catalysed, Heck, alkene + organyl halide      42—43
Coupling, Pd(0)-catalysed, Stille, aryl triflate + organostannane      42 295
CPG = controlled-pore glass particles      221
Cram’s rules      106—107
Crotonaldehyde      see “2-Butenal”
Crowding      see “Sterical strain due to crowding”
Cryptands      247—248
CSI      see “Sulfuryl chloride isocyanate”
Cubane = $pentacyclo[4.2.0.0^{2,4}.0^{3,8}.0^{4,7}]octane$ , rearrangements      332
Cubane = $pentacyclo[4.2.0.0^{2,4}.0^{3,8}.0^{4,7}]octane$ , synthesis      78
Cuneane = $pentacyclo[3.3.0.0^{2,4}.0^{3,7}.0^{6,8}]octane$       332
Cuprates(1-), alkanediyldi-, coupling with      20
Cuprates(1-), diorganyl-      5
Cuprates(1-), diorganyl-, alkylation with, of $\alpha,\beta$ -unsaturated carbonyl compounds      20—21 277
Cuprates(1-), diorganyl-, alkylation with, of 2-alkynoic acids      64
Cuprates(1-), diorganyl-, alkylation with, of carboxylic acid halides      46
Cuprates(1-), diorganyl-, alkylation with, of cyclopropyl ketones      276
Cuprates(1-), diorganyl-, alkylation with, of haloalkanes      19—20
Cuprates(1-), diorganyl-, alkylation with, of oxiranes      21
Cuprates(1-), diorganyl-, alkylation with, of oxiranylmethyl mesylates      125
Cuprates(1-), diorganyl-, alkylation with, of thioesters      320
Cuprates(1-), diorganyl-, alkylation with, of vinylic halides      20
Cuprates(1-), diorganyl-, enantioselective reagents      20—21
Cuprates(1-), diorganyl-, relative reactivity of substrates to      19—20
Curtius degradation      139 143 301 308 331.
Cyanide anion, $d^{1}$ -synthon      2 6 18 44 50 66 199 301 302
Cyanide anion, basicity      6
Cyanide anion, catalyst for the oxidation $\mathrm{RCHO\rightarrow RCOOH}$ - via acyl cyanides      134—135
Cyanoborohydride      see “Borate(1-) cyanotrihydro-”
Cyanogen bromide, cleavage of tert. amines      309
Cyanohydrins      see “Nitriles
Cyclic compounds      see “Carbocycles” “Heterocycles”
Cyclizations      see “Carbocycles” “Heterocycles”
Cyclizations, $16\pi$ -electrocyclization (thermal antarafacial)      262
Cyclizations, $18\pi$ -electrocyclization (thermal antarafacial)      334
Cyclizations, $4\pi$ -electrocyclization (thermal antarafacial), vinylcyclopropane-cyclopentene rearr.      77 83
Cyclizations, $6\pi$ -electrocyclization (photochem. antarafacial or thermal suprafacial) in alkaloid synthesis      295—296
Cyclizations, $6\pi$ -electrocyclization (photochem. antarafacial or thermal suprafacial), hexatriene-cyclohexadiene rearr.      331—332
Cyclizations, $6\pi$ -electrocyclization (photochem. antarafacial or thermal suprafacial), meta-cyclophane cyclization      38 338
Cyclizations, acid-catalysed      90—92 93 278—280 309
Cyclizations, butadiene-cyclobutene rearr. (photochem. suprafacial)      78 331
Cyclizations, cyclopropylmethanimine-dihydropyrrole rearr.      298—299
Cyclizations, cyclopropylmethanimine-dihydropyrrole rearr., pentadienylium-cyclopentenylium rearr.      258
Cyclizations, favored ring sizes in porphyrin synthesis      252—253
Cyclizations, favored ring sizes in porphyrin synthesis, stepwise      254—257
Cyclizations, favored ring sizes of butadiene (Ni template)      41
Cyclizations, favored ring sizes of diterminal diynes      40 155 339
Cyclizations, favored ring sizes, acid-catalysed cyclizatioin transforms and 1,5-enynes      90—92 279—281
Cyclizations, favored ring sizes, classic a+d or r+r ring closures      23—24 41 48 52 53—54 55 71—74 81 93 145—146 315—316 318
Cyclizations, favored ring sizes, classic a+d or r+r ring closures, Baldwin rules      315—316
Cyclizations, favored ring sizes, cyclooligomerization of alkynes      80 281 329—330
Cyclizations, favored ring sizes, template cyclizations      248 257 260 262
Cyclizations, [1+2]cycloadditions, aziridination      154 212—213
Cyclizations, [1+2]cycloadditions, cyclopropanation      74—76 94
Cyclizations, [2+2+2]cyclotrimerization of alkynes      80 281 330
Cyclizations, [2+2]cycloadditions, $\beta$ -lactams      153
Cyclizations, [2+2]cycloadditions, 1,2-oxaphosphetanes      29—30
Cyclizations, [2+2]cycloadditions, 2,2-dichlorocyclobutanones      83 276
Cyclizations, [2+2]cycloadditions, cyclobutanes      78 297—298 333
Cyclizations, [2+2]cyclodimerization of alkynes      329—330
Cyclizations, [2+3]cycloadditions of 1,3-dipoles to multiple bonds      152—153
Cyclizations, [2+3]cycloadditions of TosMIC to carbonyl groups      49 51
Cyclizations, [2+3]cycloadditions of “trimethylenemethane” to alkenes      84
Cyclizations, [2+4]cycloadditions      see “Diels — Alder reaction”
Cycloadditions      see “Cyclizations”
Cycloalkane rings      see “Carbocycles”
Cyclobutabenzenes      see “Bicyclo[4.2.0]octa-1
Cyclobutane derivs.      see “Carbocycles 4-membered”
Cyclobutanone, 2-hydroxy-, synthesis      54
Cyclobutanones, synthesis      77 79 335—336
Cyclobutene, synthesis      142
Cyclobutenes, perhalogenated, synthesis      78
Cyclobutenes, perhalogenated, thermal opening      53—54
Cyclocarbons $\mathrm{C_{6n}}$ (n=3, 4, 5), MS detection      339
Cyclodecyne, redn. of, E:Z ratio      100—101
Cyclodiphosphathiane      see “Dithiadiphosphetane”
Cyclododecanone, pr.      191
Cyclododecanone, reaction with $\mathrm{LiCHCl_{2}}$       52
Cyclododecyne, redn. of, E:Z ratio      100—101
Cyclohexanamines, N-alkylidene-, lithiated      12 56—57
Cyclohexane derivs.      see “Carbocycles 6-membered”
Cyclohexanol, 2,3-dimethyl-, pr.      189
Cyclohexanol, 2,3-dimethyl-, synthesis with      206
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, $(-)-[1R-(1\alpha,2\beta,5\alpha)]$ - (menthol), asymm. induction with      59
Cyclohexanol, 5-methyl-2-(1-methylethyl)-, $(-)-[1R-(1\alpha,2\beta,5\alpha)]$ - (menthol), pr.      189
Cyclohexanone, 2-methyl-, pr.      190
Cyclohexanone, 2-methyl-, red. elimn. of tosylhydrazone      141—142
Cyclohexanone, 2-methyl-, regioselective Robinson anellation      73
Cyclohexanone, 2-methyl-, synthesis via enamines      25—26
Cyclohexanone, 2-methyl-, synthesis via SAMP-hydrazone (enantiosel.)      25—26
Cyclohexanone, 2-methyl-, trans-6-alkylation      12
Cyclohexanone, 4-(1,1-dimethylethyl)-, ax-eq selectivity tests with      44—45
Cyclohexanone, 4-(1,1-dimethylethyl)-, pr.      190
Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (+)-(R)- ((+)-pulegone), pr.      190
Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (+)-(R)- ((+)-pulegone), pr., Favorskii rearr. of      84 211
Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (+)-(R)- ((+)-pulegone), pr., reduction of      106
Cyclohexanone, azine = cyclohexylidenehydrazone      35
Cyclohexanone, pr.      190
Cyclohexanone, spiroanellation of      24
Cyclohexanones, oxidative ring opening      82 137 195 206
Cyclohexanones, pr.      190
Cyclohexanones, synth. from alkoxyarenes      87 103—104 278
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (-)-(S)- (limonene), pr.      190
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (-)-(S)- (limonene), regioselective reactions, epoxidation      124 156—157
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (-)-(S)- (limonene), regioselective reactions, hydroboration      130—131
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (-)-(S)- (limonene), regioselective reactions, hydrogenation      101
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (-)-(S)- (limonene), regioselective reactions, ozonolysis      87—88 156—157
Cyclohexene, oxidative ring contraction      130
Cyclohexene, pr.      189
Cyclohexenes, ox. opening      81—82 87—89

Cyclohexenes, ox. ring contraction      81—82 130
Cyclononyne, redn. of, E:Z ratio      100—101
Cyclooctene, (-)-(E)-, synthesis      142
Cyclopentadecanone, 3-methyl- (muscone), $(\pm)$ -, synthesis      41
Cyclopentane derivs.      see “Carbocycles 5-membered”
Cyclopentanecarboxaldehydes      130
Cyclopentanecarboxylic acids      83—84 211
Cyclopentanecarboxylic acids, 2-oxo-, esters, pr.      189
Cyclopentanecarboxylic acids, 2-oxo-, esters, synthesis by intramolecular condensations      3 55 59 81 82 83
Cyclopentanellations      see “Carbocycles 5-membered”
Cyclopentanone in $\mathrm{C_{5}}$ -homologization of carobxylic acids      88
Cyclopentanone, 2-methyl-, enolization      11 63
Cyclopentanone, 2-methyl-, selective 2-alkylation      63
Cyclopentanone, oxime, Beckmann rearr.      136—137
Cyclopentanone, oxime, pr.      189
Cyclopentanone, pr.      189
Cyclopentanones, synthesis      82—84
Cyclopentenes from 1,5-dioxo compds      41
Cyclophanes of porphyrins      253
Cyclopropane derivs.      see “Carbocycles 3-membered”
Cyclopropane, 1-bromo-2-methoxy-, cis- and trans-, synthesis      74—75
Cyclopropane, 1-bromo-2-methoxy-, cis-, lithiation and reactions      70 76
Cyclopropane, methylene-, cyclobutanone from      77
Cyclopropane, methylene-, synthesis      74—75
Cyclopropanecarboxylic acids, esters, ring opening      69
Cyclopropanecarboxylic acids, esters, synthesis      74—76
Cyclopropanecarboxylic acids, pr.      189
Cyclopropanecarboxylic acids, synthesis      74—76 136
Cyclopropanes, (1-alkenyl)-, ring expansion      76 77 83
Cyclopropanes, (1-alkenyl)-, synthesis      75
Cyclopropanes, activated, ring opening      14—15 69—70 76—78 276
Cyclopropanols, 1-(haloamino)-, ring expansion to $\beta$ -lactams      77—78
Cyclopropanone, ketals, ring opening      14—15 70
Cyclopropanone, ketals, synthesis      75
Cyclopropanone, reaction with amines      77—78
Cyclopropanone, reaction with amines, synthesis      75
Cyclopropene, prepn. and cycloaddn. of      92
Cyclopropyl aldimines and ketimines, ring expansion      298—299
Cyclopropyl methyl ketone = 1-cyclopropyl-, ethanone, pr.      189
Cyclopropyl methyl ketone = 1-cyclopropyl-, synthesis      130
Cyclopropylogous (= homovinylogous) principle      15—16 69—70 76—77 288—289
Cycloreversion      see “Ring cleavage”
Cyclosteroids      288—289
Cyclotridecanone, 2-hydroxy-, synthesis      54
Cyclotrisilathiane, 2,2,4,4,6,6-hexamethyl-, $\mathrm{Bu^{t}Me_{2}SiSLi}$ reagent from      169
Cycloundecyne, redn. of, E:Z ratio      100—101
D-Gluconamide, N-(6,8-tetradecadiynyl)-, aqueous suspension, tubular micelles      353
D-Gluconamide, N-octyl-, aqueous suspension, helical fiber micelles      352
d-Orbitals of Si, P, S etc., carbanion stabilization      6—9
d-Orbitals of Si, P, S, carbanion stabilizn.      6—9
D-Ribonic acid, esters, D-psicosides from      272
d-Synthons      see “Donor synthons”
d.e.      see “Diastereomeric excess”
Darzens reaction      45
DAST = (N-ethylethanaminato)trifluorosulfur ( $\mathrm{Et_{2}NSF_{3}}$ )      269—270 272
dATP      see “2'-Deoxynucleoside 5'-triphosphates”
Davison nickel      see “Raney $nickel^{\circledR}$ ”
DBN      see “1
DCG      see “Carbodiimide dicyclohexyl-”
dCTP      see “2'-Deoxynucleoside 5'-triphosphates”
DDQ      see “1 4
Deblocking      154—167
Deblocking of 1,2-diols, acetonides      265 267 277 323
Deblocking of 1,3-diols, acetonides      323
Deblocking of 1,3-diols, benzylidene acetals      268—269 326
Deblocking of 1-alkynes (1-silylated)      155 339
Deblocking of carbon-carbon double bonds, $\beta$ -iodo ethers      326—327
Deblocking of carbon-carbon double bonds, 1,2-dihalides      119 156—157
Deblocking of carbon-carbon double bonds, 1,2-diols      142
Deblocking of carbon-carbon double bonds, oxiranes      157
Deblocking of carbonyl groups, acetals      130 165—166 291 328—329 339 349
Deblocking of carbonyl groups, alkenes (ozonolysis)      322 323
Deblocking of carbonyl groups, dicyanomethylene derivs.      166
Deblocking of carbonyl groups, dithioacetals      22 51 79 156 165 267 328—329
Deblocking of carbonyl groups, enol ethers      48—49 54 278
Deblocking of carbonyl groups, monothioacetals      76 165—166
Deblocking of carboxy groups      165
Deblocking of carboxy groups, 1,1-dimethylethyl esters      307
Deblocking of carboxy groups, alkyl esters      37 274
Deblocking of carboxy groups, silyl esters      313
Deblocking of enolates (with RLi), enol acetates      57—58
Deblocking of enolates (with RLi), enol silyl ethers      57—58 73
Deblocking of hydroxy groups      see “Nucleotides”
Deblocking of mercapto groups      169 229 239—240
Deblocking of methylene groups      109 155—156
Deblocking of phenols, methyl ethers      280
Deblocking of phenols, phenylmethyl ethers      305
Deblocking of phosphates      166—167 216—220 224 342
Deblocking of prim, amino groups (labile amides)      161—164 216—218 224 229 235—240 267 342
Deblocking of sec. amino groups, acetamides      304
Deblocking of sec. amino groups, carbamates      235—236 301
Deblocking of sec. amino groups, sulfonamides      247 304
Deblocking of sec. amino groups, tert. amines (cleavage with BrCN)      309
Deblocking of tert. amino groups, thermal dequaternization      304
Deblocking, acetate esters etc.      157—158 266—269 271 273 282 283
Deblocking, acetate esters etc., $\beta$ -iodo ethers      326—327
Deblocking, acetate esters etc., (1,1-dimethylethyl)dimethylsilyl ethers      62 157 159 276—277 281 323 328 329
Deblocking, acetate esters etc., (1,1-dimethylethyl)diphenylsilyl ethers      272
Deblocking, acetate esters etc., (4-methoxyphenyl)methyl (= MPM = PMB) ethers      157 325—329
Deblocking, acetate esters etc., 1,1-dimethylethyl (t-butyl) ethers      280 283
Deblocking, acetate esters etc., 2,2,2-trihaloethyl carbonates      157—158
Deblocking, acetate esters etc., 2-propenyl (allyl) ethers      270
Deblocking, acetate esters etc., 9-phenyl-9H-xanthan-9-yl (pixyl) ethers      342
Deblocking, acetate esters etc., dialkylborinate esters      60—62 67—68
Deblocking, acetate esters etc., enantiotoposelective      167—168 276—277
Deblocking, acetate esters etc., methyl ethers      157 161 275
Deblocking, acetate esters etc., phenylmethyl (benzyl) ethers      157—159 161 229 271 328
Deblocking, acetate esters etc., tetrahydro-2H-pyran-2-yl (THP) ethers      82 157 159—160 273
Deblocking, acetate esters etc., trimethylsilyl ethers      83 159 275 281
Deblocking, acetate esters etc., triphenylmethyl (trityl) and related ethers      216 218—222 224
Decalin      see “Naphthalene decahydro-”
Decanoic acid, 10-oxo, methyl ester, olefination of      31
Decarboxylation      139
Decarboxylation of $\beta$ -oxo carboxylic acids      81—83 139 195
Decarboxylation of $\beta,\gamma$ -unsatd. $\delta$ -lactones      80 92 331
Decarboxylation of $\delta$ -oxo $\beta,\gamma$ -unsatd. acids      209—210 331
Decarboxylation of diarylacetic acids      303
Decarboxylation, oxidative, of $\alpha$ -amino acids      48
Decarboxylation, oxidative, of 1,2-dicarboxylic acids      80 142 333 337
Decarboxylation, oxidative, of carboxylic acids to amines      139 143 301 308 331
Dehydrogenation      122 138—140
Dehydrogenation of porphyrinogens      251—253 349
Dehydrogenation, aromatization, with Pd      337
Dehydrogenation, aromatization, with trityl cation      249 334
Dehydrogenation, exhaustive      139—140 338
Dendrimers = dendritic polymers      354—356
Deoxygenation of N-, P- and S-oxides      115
Deoxyribonucleic acid      see “DNA”
Deoxysulfonation, reductive      34
Deprotection      see “Deblocking”
Deprotonation      see “Bases”
Depurination, undesired side-reaction      222
Desilylation      see “Deblocking”
Dess — Martin periodinane (BMP)      134 328—329
Desulfurization      see “Sulfones” “Thiiranes” “Thioethers”
Desymmetrization, diastereotoposelectjve      168
Dewar benzenes = bicyclo[2.2.0]hexa-2,5-dienes      330
Dexbrompheniramine      303
Dextropropoxyphene      300
dGTP      see “2'-Deoxynucleoside 5'-triphosphates”
DHP      see “2H-Pyran 3
Diademane = octahydro-1,2,3-methano-1H-dicycloprop[cd,hi]indene      333
Dialdehydes by ox. cleavage of cycloalkenes      81—82 87—88
Dialdehydes from diones + $\mathrm{LiCHCl_{2}}$       51—52
Diastereo-zeroplane, definition      360
Diastereofaces, definition      360
Diastereomeric excess = diastereoselectivity, definition, prelim. (footnote d.e. = d.s. = % (l)-isomer-% (u)-isomer)      XIII 107
Diastereoselectivity      see “Asymmetric induction” “Axial/equatorial-selectivity” “cis/trans-selectivity” “endo/exo-selectivity” “erythro/threo-selectivity” “Inversion” “Retention”
Diastereoselectivity, diastereotopic face selectivity      126—127
Diastereoselectivity, diastereotopic group selectivity      168 360

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