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

Reductive cleavage      see “Hydrogenolysis” “Ring
Reductive cleavage of alcohols      97 113—114 202—203 277
Reductive cleavage of haloalkanes      see “Reduction”
Reductive cleavage of ketone derivs.      109 114—115 155—156
Reductive cleavage of nitriles (decyanation)      280
Reductive cleavage of peroxides      276—277
Reductive cleavage of protecting groups      156—159 162—165 167
Reductive cleavage of steroids with 10-alkyl      287—288
Reductive cleavage of sulfonamides      247
Reductive cleavage of sulfones      70
Reductive cleavage of thioethers      26 39 76 82 98 109 110—111 113—114 156 273
Reductive cleavage of tosylhydrazones      109 141—142
Reductive coupling of alkenes via boranes      37
Reductive coupling of alkynes via boranes      37—38
Reductive coupling of allylic halides via Ni complexes      42
Reductive coupling of allylic halides via thioethers      39
Reductive coupling of carbonyl compounds with arylic esters, $\mathrm{SmI_{2}}$       69
Reductive coupling of carbonyl compounds, acyloin coupling      53—54
Reductive coupling of carbonyl compounds, Barton olefination      35
Reductive coupling of carbonyl compounds, McMurry olefination      41
Reductive coupling of carbonyl compounds, pinacol coupling      53
Reductive coupling of haloalkanes      36
Reductive coupling of nitroarenes      305
Reductive deoxysulfonatibn      34
Reductive desulfurization      see “Sulfones” “Thiiranes” “Thioethers”
Reductive ring opening      see “Ring opening”
Reetz reagent ( $\mathrm{Me_{2}Zn/TlCl_{4}}$ 5:1)      21
Reformatsky reaction of $\alpha$ -bromo carboxylic esters      44—45 301
Reformatsky reaction of allylic bromides      44—45
Regioselectivity of aldol type reactions      55—58 93 318
Regioselectivity of alkylations of $\pi$ -allylpalladium complexes      27
Regioselectivity of alkylations of 1,3-dioxo dianions      9—10 24 204 326
Regioselectivity of alkylations of enamines      13—14 25—26
Regioselectivity of alkylations of oxiranes      21 44 64
Regioselectivity of alkylations, $\alpha$ or $\alpha'$ of $\alpha,\beta$ -unsatd. ketones      25
Regioselectivity of alkylations, $\beta$ of $\alpha,\beta$ -unsatd. ketones      20—21
Regioselectivity of amination of $\pi$ -allylpalladium      164
Regioselectivity of Baeyer — Villiger oxidation      136—137
Regioselectivity of cyclopropanations      75—76
Regioselectivity of enolization of $\alpha,\beta$ -unsaturated ketones      25 58
Regioselectivity of enolization of ketones      11—13 57—58
Regioselectivity of halohydrinations      77 160 275—276 286 287
Regioselectivity of halolactonization      275 319—320 335—336
Regioselectivity of heterocycle syntheses      149—153 291—298 307—309
Regioselectivity of hydration of alkynes with Hg(2+)      52 57
Regioselectivity of hydroborations      37—38 47—48 89—90 107—108 130—131 319—320
Regioselectivity of hydrozirconations      132
Regioselectivity of Michael type additions      71—74 318
Regioselectivity of ox. cleavage of arenes and dienes      87—88
Regioselectivity of oxidation of alkenes      118—119 285—286
Regioselectivity of oxidation of allylic CH      119—121
Regioselectivity of oxidation of dienes      82 123—124 126—129 156—157
Regioselectivity of oxidation, $\alpha$ of ketones      121—122
Regioselectivity of protection of functional groups      154—167
Regioselectivity of reduction of $\alpha,\beta$ -unsaturated carbonyl compounds, C=C reduction      73 103—104 322—323
Regioselectivity of reduction of $\alpha,\beta$ -unsaturated carbonyl compounds, C=O reduction      105—107 265 273
Regioselectivity of reduction of diynes      100—101
Regioselectivity of reduction of tosylhydrazones      141—142
Regioselectivity of ring expansion of ketones with $\mathrm{CH_{2}N_{2}}$       83
Regioselectivity of [2+2]cycloadditions      78 276 297—298
Regioselectivity of [2+4]cycloadditions      85—86
Remote oxidation      116 118 285—286
Resin, anion exchange      see “Hunig base polymeric”
Resin, cation-exchange      see “Sulfonic acids”
Resolution of racemats      see “Optical resolution”
Resorcinols      see “1
Restriction endonucleases      243
retention      see “Racemization prevention
Retention of cis/trans- or -R/S-con figuration, organyl coupling of boranes      37—38
Retention of cis/trans- or -R/S-con figuration, organyl coupling of cuprates      20
Retention of cis/trans- or -R/S-con figuration, ox. cleavage of triorganylboranes      130—131
Retention of cis/trans-configuration, alkylation of vinylic halides      20
Retention of cis/trans-configuration, amination of allyl acetates via allyl-Pd      164
Retention of cis/trans-configuration, Baeyer — Villiger oxidations      136—137
Retention of cis/trans-configuration, fragmentations      89—90
Retention of cis/trans-configuration, hydrolysis of triorganylboranes      37—38
Retention of cis/trans-configuration, [1+2]cycloadditions      75
Retention of cis/trans-configuration, [2+4]cycloadditions      85—86 280—281 297
Retention of R/S-configuration, $\alpha$ -alkylation of N,O-protected proline      299
Retention of R/S-configuration, 1-alkylation of carboxylic acid derivs.      46
Retention of R/S-configuration, alkylation of allyl acetates via $\pi$ -allyl-Pd      27
Retention of R/S-configuration, diazotization of ec-amino acids      202—203
Retention of R/S-configuration, displacement of OH. $\mathrm{SOCl_{2}}$ , $\mathrm{PCl_{5}}$       288—289
Retention of R/S-configuration, glycosylation, 2-O-acyl neighboring group participation      270—271
Retention of R/S-configuration, oxidation of benzylic CH      120
Retinal $\beta$ -carotene from      41
Retinol (vitamin A), acetate, synthesis      31
Retro-aldol type cleavage      see “Decarboxylations”
Retro-aldol type cleavage of 1,3-dioxo compounds      81 88 207
Retro-aldol type cleavage of 17-(methoxyoxoacetyl) chlorin      259
Retro-aldol type cleavage of pyrroles in Knorr’s synthesis      150—151
Retro-aldol type transform      194
Retro-Diels — Alder type cleavage, $\mathrm{CO_{2}}$ elimination by      80 92 331
Retro-Diels — Alder type cleavage, $\mathrm{SO_{2}}$ elimination by      80 153
Retro-Diels — Alder type cleavage, CO elimination by      337
Retro-Diels — Alder type transform      194 210 212
retro-Synthesis      see “Retro-synthetic analysis”
Retro-synthetic analysis      171 193—213
Retro-synthetic analysis, commercial starting materials      171—192
Retro-synthetic analysis, enantioselective      200—204
Retro-synthetic analysis, exercises      213—214
Retro-synthetic analysis, symbols and terminology      193—196
Reverse transcriptase      242
Rhodium(1+) complexes, [2+2]cycIoreversion of cyclobutanes      332
Rhodium(1+), chiral “binap” complexes, asymmetric hydrogenation with      102—103
Rhodium(1+), tris(triphenylphosphine)-, hydroboration catalyst      131
Ribonucleic acid      see “RNA”
Ring cleavage, electrocyclic (cycloreversion), [1+1+2]-, double CO elimination      78 339
Ring cleavage, electrocyclic (cycloreversion), [1+4]-, $\mathrm{SO_{2}}$ elimination      80 153
Ring cleavage, electrocyclic (cycloreversion), [1+4]-, CO elimination      337
Ring cleavage, electrocyclic (cycloreversion), [2+2+2]-, diademane opening      333
Ring cleavage, electrocyclic (cycloreversion), [2+2]-, benzene elimination      331 332—333
Ring cleavage, electrocyclic (cycloreversion), [2+2]-, prismane opening      330—331
Ring cleavage, electrocyclic (cycloreversion), [2+2]-, rhodium(1+)-catalysed      332
Ring cleavage, electrocyclic (cycloreversion), [2+2]-, thermal      79—80
Ring cleavage, electrocyclic (cycloreversion), [2+4]-, $\mathrm{CO_{2}}$ elimination      80 92 331
Ring closure      see “Cyclization”
Ring contraction by extrusion of carbon dioxide      80
Ring contraction by extrusion of carbon monoxide      330
Ring contraction by extrusion of molecular nitrogen      35 331 334
Ring contraction by extrusion of sulfur      38—39 338
Ring contraction by extrusion of sulfur dioxide      80
Ring contraction by Favorskii rearrangement      78 84 211
Ring contraction by oxn. of cycloalkenes with Tl(3+)      129—130
Ring contraction by pinacol rearrangement      32
Ring contraction by Wolff rearr. of $\alpha$ -diazo ketones      337
Ring contraction via ox. cleavage of cyclic ketones      82
Ring contraction via ox. cleavage of cycloalkenes      81—82
Ring expansion, 1,4-benzodiazepinedruns      307
Ring expansion, cationic, of 1,2-diols      32
Ring expansion, cationic, of cyclopropanes      76—78 79 83
Ring expansion, cationic, of ketones with $\mathrm{CH_{2}N_{2}}$       83
Ring expansion, cationic, of penams to cephams      314 315
Ring expansion, electrocyclic, by 1,2-cyclohexadiene opening      332—334
Ring expansion, electrocyclic, by cyclobutene opening      53—54
Ring expansion, electrocyclic, of cyclopropanemethanimines      298—299
Ring expansion, electrocyclic, of vinylcyclopropanes      77 83
Ring expansion, fragmentation of fused ring systems      89—90
Ring expansion, ozonolysis and re-cyclization      91—92 280
Ring expansion, reduction of cyclopropanes      76
Ring expansion, transamidation (”zip” reaction)      249—250
Ring opening, base-catalysed, of 4-tosyl-2-oxazolines      49
Ring opening, base-catalysed, of cyclopropanols (”homoenolates”)      77
Ring opening, electrocyclic, of 1,3-cyclohexadienes      289 332 334
Ring opening, electrocyclic, of cyclobutenes      53—54 330—331
Ring opening, fragmentative      89—90 141—142
Ring opening, Lewis acid catalysed, of cyclopropanone ketals      14—15 70
Ring opening, nucleophilic, of 1,2-dione mono(dithioketals)      79
Ring opening, nucleophilic, of cyclopropanes      14—15 69—70 76—77 83—84 276
Ring opening, nucleophilic, of oxiranes      see “Oxiranes”

Ring opening, oxidative, of 1,2-arenediol derivs.      87—88
Ring opening, oxidative, of cyclic ketones      79 82 136—137
Ring opening, oxidative, of cyclic thioethers      314—315
Ring opening, oxidative, of cycloalkenes      81—82 87—88 259 280
Ring opening, oxidative, of tert-cycloalkanols      136
Ring opening, reductive, of cyclopropanes      76 105
Ring opening, reductive, of oxiranes      98 114 274—275 319—320
Ring opening, retro-aldol type      88
Ring sizes, favored      see “Cyclizations”
Robinson anellation      71—73 93
Robinson anellation of enamines      298
Robinson anellation with $\alpha$ -amines activated enones      73
Rolitetracyciine      318
Rose Bengal, xanthene dye, photosensitizer      277
Ruthenium(2+), chiral “binap” complexes, asym. hydrogenation with      102—103 325—326
Ruthenium(8+) oxide, oxidation with, of alcohols to ketones (catalytic)      267
Ruthenium(8+) oxide, oxidation with, of alkynes to 1,2-diones (catalytic)      117 132
Ruthenium(8+) oxide, oxidation with, of ethers to esters      118 134—135
Ruthenium, dihydrotetrakis(triphenylphosphine)-, double bond shift in alkenes      270
S1 Nuclease      242
Sakurai reaction, Michael type allylation      90
Samarium(2+) iodide ( $\mathrm{SmI_{2}}$ ), deoxygenation of distannoxanes      135
Samarium(2+) iodide ( $\mathrm{SmI_{2}}$ ), deoxygenation of N-, P-, and S-oxides      115
Samarium(2+) iodide ( $\mathrm{SmI_{2}}$ ), red. coupling of aldehydes or ketones with acrylic esters      69
SAMP = (S)-2-(methoxymethyl)-1-pyrrolidinamine      26
Sand-sodium base      see “Sodium-sand base”
Schering process      118—119
Schiff bases      see “Imines”
sec. Amines, N-halo-, Stieglitz rearr.      77—78
sec. Amines, synthesis by hydrolysis of tert. carboxamides      301
sec. Amines, synthesis by reduction of sec. carboxamides      98 111—112 247
sec. Amines, synthesis by reduction of W-alkylimines      302
sec. Amines, synthesis by reductive detosylation      247
Seebach-Frater alkylation      27
Selenium(4+) oxide ( $\mathrm{SeO_{2}}$ ), dehydrogenation with      122 138 139
Selenium(4+) oxide ( $\mathrm{SeO_{2}}$ ), oxidation with, of allylic CH      116 119—120
Selenium(4+) oxide ( $\mathrm{SeO_{2}}$ ), oxidation with, of allylic CH, $\alpha$ of carbonyl compounds      116 122 137
Selenium(4+) oxide ( $\mathrm{SeO_{2}}$ ), reagent with $\mathrm{H_{2}O_{2}}$ (selenous peracid), Baeyer — Villiger oxidation with      136—137
Selenium, phenyl-, bromide = benzeneselenenyl bromide, dehydrogenation with      138 139
Self-replication mechanisms in synthetic molecular complexes      347—348
Semibullvalene = 2a,2b,4a,4b-tetrahydrocyclopropa[cd]pentalene      331—332
Separation of enantiomers      see “Optical resolution”
SFS (sodium formaldehyde-sulfoxylate)      see “Methanesulfinic acid hydroxy-”
Sharpless epoxidation      124—127 265 321—325
Sheehan’s oxazolone protecting group      161 164
Silanamine, 1,1,1-trimethyi-N-(trimethylsiiyl)- (hexa-Si-methyldisilazane, $\mathrm{(Me_{3}Si)_{2}NH}$ , HMDS), catalyst for $\beta$ -elimination of sulfoxides      315
Silanamine, 1,1,1-trimethyi-N-(trimethylsiiyl)- (hexa-Si-methyldisilazane, $\mathrm{(Me_{3}Si)_{2}NH}$ , HMDS), sodium salt (HmdsNa), deprotonation with, of alkyiphosphonium salts      31
Silanamine, 1,1,1-trimethyi-N-(trimethylsiiyl)- (hexa-Si-methyldisilazane, $\mathrm{(Me_{3}Si)_{2}NH}$ , HMDS), sodium salt (HmdsNa), deprotonation with, of carbonyl compounds      10 44
Silane, (chloromethyl)trimethyl-, metalation of      6—7
Silane, (chloromethyl)trimethyl-, Peterson olefination with      33
Silane, (chloromethyl)trimethyl-, pr.      187
Silane, chiorotrimethyl- ( $\mathrm{Me_{3}SiCl}$ ), pr.      187
Silane, chiorotrimethyl- ( $\mathrm{Me_{3}SiCl}$ ), protection with      see “Protection”
Silane, ethenyltriphenyl-, carbanion addn. to      34
Silane, iodotrimethyl-, O-fert-butyl deblocking      283
Silane, trimethyl(2-propenyl)-, allyl $d^{3}$ -synthon      90
Silane, [(1-ethoxycyclopropyl)oxy]trimethyl-, $d^{3}$ -synthon      15 70
Silane, [(1-ethoxycyclopropyl)oxy]trimethyl-, synthesis steps      75
Silanes      see “Protection”
Silanes, ( $\beta$ -oxoalkyl)-, desilylation with bases      73
Silanes, (1-alkenyl)-, carbanion addn. to      6—7 34
Silanes, (2-aIkenyl)-, ailyl $d^{3}$ -synthons      90
Silanes, aryl-, acidolysis      80 281
Silanes, aryl-, oxidative cleavage with $\mathrm{Br_{2}}$       80
Silanes, tetraorganyl-, a-carbanions      6—7 33—34
Silanethiol, (1,1-dimethyiethyl)dimethyl-, Li salt, conversion of haloalkanes to thiols      169
Silicon compounds, pr.      187
Silver(1+) carbonate, $\mathrm{RCH_{2}OH\rightarrow RCHO}$       133
Silver(1+) nitrate ( $\mathrm{AgNO_{3}}$ ), deprotection of 1-silyl-1-alkynes      155
Silver(1+) nitrate ( $\mathrm{AgNO_{3}}$ ), oxidative organyl coupling at $\mathrm{R_{3}B}$       37
Silver(1+) oxide ( $\mathrm{Ag_{2}O}$ ), oxidative organyl coupling at $\mathrm{R_{3}}B$ for O-benzylation      157 158
Silver(1+) oxide ( $\mathrm{Ag_{2}O}$ ), oxidative organyl coupling at $\mathrm{R_{3}}B$ for oxidative coupling of enol silyl ethers      65
Silver(1+) silicate on aluminum oxide, reagent for inversion-glycosylation      271
Silver(1+) with $\mathrm{SnCl_{2}}$ , $\mathrm{CP_{2}ZrCl_{2}}$ or $\mathrm{Cp_{2}HfCl_{2}}$       270
Silver(1+), oxn. of alkenes, $\mathrm{Ag^{+}/I_{2}/RCOOH}$       127—128
Silver(1+), rearr. of 1-(chloroamino) alcohols      77—78
Silver(1+), rearr. of strained oligocycles      79—80 332—333
Silver(1+), transesterification of thioesters      146
Silvet(2+), oxide, oxn. $RCHO\rightarrow RCOOH$       134
Silyl ethers      see “Protection”
Simmons-Smith reaction      74—75 83
Sirenin, $(\pm)$ - = $(1\alpha,6\alpha,7\alpha)$ -7-(5-hydroxy-4-methyl-3-pentenyl)-7-methylbicyclo[4.1.0]hept-2-ene-3-methanol, synth. step      20
Site-specific DNA cleavage      243 343—344
Site-specific DNA mutations      245—246 341—343
Snoutene = 2,2a,2b,3,5a,5b-hexahydro-1,2,3-metheno-1H-cycloprop[cd]indene      333
Soccerene = fullerene      357
Sodium amalgam, reductive desulfurization of sulfones      70
Sodium amalgam, reductive elimination of $\beta$ -acyloxy sulfones      34
Sodium borohydride      see “Borate(1-) tetrahydro-”
Sodium, acyloin coupling with      53—54
Sodium, haloalkane (Wurts) couphng with      36
Sodium, reduction with      see “Birch reduction”
Sodium, reductive cleavage of benzyl ethers      157—159
Sodium, reductive cleavage of “Ox”-protected amines      164
Sodium-complex or organic salts      see corresponding acid or anion
Sodium-naphthalene reagent, reductive deblocking with      220
Sodium-sand base, non-nucleophilic base      58—59
Solid-phase synthesis of macrocyclic peptides      241
Solid-phase synthesis of oligonucleotides      221—224 341—343
Solid-phase synthesis of oligopeptides      232—237
Soret UV/VIS absorption band of porphyrins, shifts due to aggregation      348 349
Spiroanellation of $\alpha$ -methylene groups of carboxylic acid derivs.      23—24 298 300
Spiroanellation of $\alpha$ -methylene groups of ketones      27 74
Spiroanellation of ketones with Trost’s reagent      79 335—336
Spiroanellation, Diels — Alder type      86
Spiroanellation, intramol. alkene coupling in Fe complexes      44
Squalene, 18,19-glycol 2,3-oxide, acid-catalysed cyclisation of      91
Squalene, biological role      90 279 302
Squalene, pr.      186
Squaric acid      78
Squaric acid dichloride      339
Stannane, tributyl-, reduction of haloalkanes      97 114—115 275 319—320
Stannane, triphenyl-, red. desulfurization of thioethers      110—111
Stannanes, (1-alkenyl)-, synth. from alkynes      321
Stannanes, (1-alkenyl)-, transmetalation with MeLi      322—323
Stannanes, (2-alkenyl)-, 1-allylation of aldehydes      66—67 325—326
Stannanes, (2-alkenyl)-, allylation of bromoboranes      68—69
Stannanes, Stille coupling with      42 295
Stannoxanes, deoxygenation      115
Starburst dendrimers      354—355
Stereoelectronic control      see “Electrocyclic reactions”
Stereoelectronic control, $\beta$ -lactam stability      311—315
Stereoelectronic control, fragmentation reactions      89—90
Stereoelectronic control, nucleophilic cyclizations      315—316
Stereoelectronic control, ox. cleavage of cyclic thioethers      314—315
Stereoelectronic control, prevention of $\beta$ -eHmination      265
Stereoelectronic control, prevention of enolate formation      277
Stereoelectronic control, prevention of racemization      231 299
Stereoelectronic control, reduction of $\alpha,\beta$ -unsatd. ketones      103—104
Stereoselective retro-synthetic analysis      200—204 206 209—211
Stereoselective retro-synthetic analysis, chiral synthons = “chirons”      202—203 211 272—273
Stereoselectivity      see “Asymmetric induction” “Axial/equatorial-Selectivity” “cis/trans-Selectivity” “Enantio-Selectivity” “endo/exo-Selectivity” “erythro/threo-Selectivity” “Inversion” “Retention”
Stereoselectivity, definition (e.e.)      107 footnote
Steric hindrance, overcoming of, in acylations      145
Steric hindrance, overcoming of, in aldol type reactions      55—56
Steric hindrance, overcoming of, in corrin synthesis      261—262
Steric hindrance, overcoming of, in Diels — Alder cyclizations      86
Steric hindrance, overcoming of, in Michael type additions      90
Steric hindrance, overcoming of, in olefinations, Barton olefination      34—35
Steric hindrance, overcoming of, in olefinations, McMurry olefination      41
Steric hindrance, overcoming of, in olefinations, Peterson olefination      33
Steric hindrance, overcoming of, in syntheses of $\alpha$ -hydrdoxy ketones      52
Steric strain due to bridges (Bredt’s rule), effect on enolization      276 277 296 299
Steric strain due to bridges (Bredt’s rule), effect on p-lactam stability      311—315
Steric strain due to crowding, release of, in chlorophyll synthesis      258—259
Steric strain due to crowding, release of, in dodecahedrane synthesis      336—337
Steric strain due to crowding, release of, in meta-cyclophane rearrangement      38 338
Steric strain due to crowding, release of, in prismane synthesis      330
Steric strain due to crowding, release of, in tetrahedrane synthesis      330
Steric strain due to small angles, release of      79—80 330—333 337 3-membered” “Carbocycles 4-membered”)

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