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Fuhrhop J., Penzlin G. — Organic Synthesis: Concepts, Methods, Starting materials
Fuhrhop J., Penzlin G. — Organic Synthesis: Concepts, Methods, Starting materials



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Íàçâàíèå: Organic Synthesis: Concepts, Methods, Starting materials

Àâòîðû: Fuhrhop J., Penzlin G.

ßçûê: en

Ðóáðèêà: Õèìèÿ/

Ñòàòóñ ïðåäìåòíîãî óêàçàòåëÿ: Ãîòîâ óêàçàòåëü ñ íîìåðàìè ñòðàíèö

ed2k: ed2k stats

Èçäàíèå: second edition, rewise and enlarged

Ãîä èçäàíèÿ: 1994

Êîëè÷åñòâî ñòðàíèö: 432

Äîáàâëåíà â êàòàëîã: 29.10.2005

Îïåðàöèè: Ïîëîæèòü íà ïîëêó | Ñêîïèðîâàòü ññûëêó äëÿ ôîðóìà | Ñêîïèðîâàòü ID
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Ïðåäìåòíûé óêàçàòåëü
Magnesium, bromoethenyl-, Michael type ethenylation with Cu(1+)      281
Magnesium, bromoethyl-, metalation of 1-alkynes      5 155
Magnesium, chloro[(trimethylsilyl)methyl]-, Peterson olefination with      33
Magnesium, chloro[(trimethylsilyl)methyl]-, preparation      6—7
Magnesium, iodomethyl-, selective methylation      318
Magnesium, metalation of organyl halides      5 6—7 17 20 46
Malabaricanediol, $(\pm)$- and $(\pm)$-18,19-epi-      91
Maleic anhydride      see “2
Malic acid      see “Butanedioic acid 2-hydroxy-”
Malonic acid      see “Propanediol acid”
Malononitrile      see “Propanedinitrile”
Manganese(4+) oxide, oxidation with, of aldehydes via cyanohydrins      134—135
Manganese(4+) oxide, oxidation with, of allylic alcohols      133—135
Mannich bases      see “Ketones
Mannich reactions      57 291—292 300 304 310 317—318
Mannich reagents      see “Iminium ions”
Marker degradation      283/285
Martin’s sulfurane reagent, dehydration by      282
Masamune reaction, aldol addition of chiral $\alpha$-silyloxy ketones      62
McMurry olefination      41
Mcpba      see “Benzenecarboperoxoic acid 3-chloro-”
Meclizine = meclozine, $(\pm)$-      304
Meerwein — Ponndorf redn.      see “Oppenauer oxn.”
Meerwein — Ponndorf redn. with $\mathrm{CH_{2}(OH)_{2}/NaOH}$      302
Meerwein — Ponndorf redn., ax/eq equilibration of cycloalkanols      288
Meerwein’s reagents      see “Methylium dimethoxy-” “Oxonium triethyl-” “Oxonium trimethyl-”
Membranes, bilayer (BLM), from lipids or synthetic amphiphiles      350—351
Membranes, bilayer (BLM), permeability enhancement, $\mathrm{Ca^{2+}}$      243—244
Membranes, monolayer, from bola amphiphiles      351
Menthol, (-)-(1R)-, (+)-(1S)- and $(\pm)$-, asym. aldol type addition with esters of      59
Menthol, (-)-(1R)-, (+)-(1S)- and $(\pm)$-, pr.      189
Meprobamate      302
Mercury(2+) acetate, hydration of alkenes      283
Mercury(2+) acetate, oxn. of allylic or benzylic CH      116 120—121
Mercury(2+) acetate, oxn. of tert. amines      116 120—121 138—139
Mercury(2+), catalyst for alcohol addition to alkynes      64—65 325 327—328
Mercury(2+), catalyst for glycosylations (Koenigs — Knorr)      267
Mercury(2+), catalyst for hydration of alkynes      52 57 117
Mercury(2+), catalyst for hydrolysis of 1-alkenyl halides      63
Mercury(2+), catalyst for hydrolysis of dithioacetal derivs.      22 66 156 267
Mercury(2+), catalyst for hydrolysis of monothioacetal derivs.      76 229
Mercury(2+), catalyst for hydrolysis of thiocarbamates      229
Mercury(2+), catalyst for hydrolysis of trityl thioethers      229
Merrifield’s peptide synthesis      232—237
Mesembrine, $(\pm)$-      298
Mesoionic intermediates in cycloadditions      153
Mesoionic intermediates in electrocyclizations      262 295—296
Mesoporphyrin      256
Messenger-RNA (mRNA) for gene cloning      242
Mesylates      see “Methanesulfonic acid esters”
meta-Cyclophanes      38 338
Metal organyls      see “Organometallic compounds”
MethanaL      see “Formaldehyde”
Methanamine, 1,1-dimethoxy-N,N-dimethyl-, formylation with      82
Methanamine, N,N-dimethyl-, N-oxide, oxn. of $\mathrm{R_{3}B}$      37
Methane, (methylsullmylXmethylthio)- (MMTS), synthesis of ketones      66 205
Methane, chloromethoxy- ($\mathrm{ClCH_{2}OMe}$), Friedel — Crafts chloromethylation with      233
Methane, chloromethoxy- ($\mathrm{ClCH_{2}OMe}$), methoxymethylation with      210
Methane, chloromethoxy- ($\mathrm{ClCH_{2}OMe}$), O-methoxymethyl (MOM) protection      318
Methane, diazo- ($\mathrm{CH_{2}N_{2}}$), carbenoid reactions of      74—75 166 334
Methane, diazo- ($\mathrm{CH_{2}N_{2}}$), cyclopropanone synthesis with      75
Methane, diazo- ($\mathrm{CH_{2}N_{2}}$), prepn. of methyl esters with      82 325
Methane, diazo- ($\mathrm{CH_{2}N_{2}}$), ring expansion of cyclic ketones with      83
Methane, dichloromethoxy- ($\mathrm{Cl_{2}CHOMe}$), methoxycarbene from      74
Methane, dichloromethoxy- ($\mathrm{Cl_{2}CHOMe}$), pr.      179
Methane, diiodo-, carbene synthon      74—75 83
Methane, iodo-, $\alpha$-methyl lactones      321 322 328
Methane, iodo-, S-methylation of thiols      110—111
Methane, sulfinylbis[- (dimethyl sulfoxide, DMSO), acidity      10
Methane, sulfinylbis[- (dimethyl sulfoxide, DMSO), dehydration of alcohols with      140
Methane, sulfinylbis[- (dimethyl sulfoxide, DMSO), Moffatt — Pfitzner and Swern oxn. of alcohols      133—134 322—323 325—327
Methane, sulfinylbis[-, ion(1-) (”dimsyl anion”), $d^{1}$-synthon      6 8 50—51 65
Methane, sulfinylbis[-, ion(1-) (”dimsyl anion”), deprotonation with, of carbonyl compounds      10 83
Methane, sulfinylbis[-, ion(1-) (”dimsyl anion”), deprotonation with, of phosphonic diesters      30
Methane, sulfinylbis[-, ion(1-) (”dimsyl anion”), deprotonation with, of sulfonium salts      8
Methane, tetrahalo-, halides from prim, alcohols, $\mathrm{CX_{4}Ph_{3}P/Py}$ (X=Cl, Br, I)      266
Methane, tetrahalo-, halides from prim, alcohols, oxn. of phosphonic diesters, $\mathrm{HPO(OR)_{2}}$      343
Methane, tribromo-, $\mathrm{CBr_{2}}$ from      75
Methane, trichloro-, lithiated      51—52
Methane, trimethoxy      see “Orthoformic acid esters”
Methane, trimethylene- = 2-methylene-1,3-propanediyl, e-synthons for [3+2]cycloadditions      84
Methanediamine, 1-(1,1-dimethylethoxy)-N,N,N',N'-tetramethyl-, vinylogous amides from      79
Methanesulfenyl bromide (MeSBr), activation of thioglycosides      271
Methanesulfonic acid      see “Sulfonic acids”
Methanesulfonic acid, 1-cyclopropylalkyl esters, $a^{4}$-synthons      15 17 70 76
Methanesulfonic acid, 1-decalyl esters, fragmentation of      89—90
Methanesulfonic acid, alkyl esters (mesylates), a-synthons      15—17
Methanesulfonic acid, alkyl esters (mesylates), alkyl azides from      267
Methanesulfonic acid, trifluoro- (triflic acid), (1,1-dimethylethyl)dimethylsilyl ester, O-silylations with      321 322 325 328
Methanesulfonic acid, trifluoro- (triflic acid), anhydride with dibutylborinic acid (dibutylboryl triflate, $\mathrm{CF_{3}SO_{3}BBu_{2}}$) etc., boron enolates from      12—13 61—62
Methanesulfonic acid, trifluoro- (triflic acid), anhydride, triflate esters from      295
Methanesulfonic acid, trifluoro- (triflic acid), aryl esters (aryl triflates), Stille coupling with organylstannanes      42 295
Methanesulfonic acid, trifluoro- (triflic acid), catalyst for skeletal rearr.      335—336
Methanesulfonic acid, trifluoro- (triflic acid), methyl ester (methyl triflate, $\mathrm{CF_{3}SO_{3}Me}$), S-methylation of dimethyl disulfide      271
Methanesulfonic acid, trifluoro- (triflic acid), trimethylsilyl ester ($\mathrm{CF_{3}SO_{3}SiMe}$), activation of glycosyl imidates      270—271
Methanesulfonyl chloride (mesyl chloride, MsCl), prepn. of mesylate esters      70 76 267 283
Methanesullinic acid, hydroxy-, monosodium salt (SFS), redn. of thiohemiacetals with      51
Methanoic acid      see “Formic acid”
Methanol, ion(1-), deblocking of O-acyl derivs.      157—158 160 271
Methanol, ion(1-), deprotonation with, of 1,3-diones      72—73
Methanol, ion(1-), deprotonation with, of ketones      84
Methanol, ion(1-), deprotonation with, of phosphonium salts      31
Methanol, ion(1-), desilylation of $\alpha$-silyl ketones with      73
Methanol, ion(1-), rearrangements of $\alpha$-halo ketones      84
Methanol, ion(1-), rearrangements of $\alpha$-halo triorganylboranes      37—38
Methanone, diphenyl-, aldol addn. with      56—57
Methionine, pr.      185
Methionine, protection      229
Methyldopa, (-)-L-      301
Methylenes      see “Carbenes”
Methylidynation, 1-alkynes from aldehydes      325
Methylium, dimethoxy-, tetrafluoroborate ($\mathrm{[(MeO)_{2}CH]BF_{4}}$), formyl $a^{1}$-synthon      58—59
Methylium, dimethoxy-, tetrafluoroborate ($\mathrm{[(MeO)_{2}CH]BF_{4}}$), S-methylation of thioethers      38
Methylium, triphenyl- ($\mathrm{[Ph_{3}C]PF_{6}}$ or $\mathrm{[Ph_{3}C]BF_{4}}$), dehydrogenation with      44 249 334
Methylphenidate, $(\pm)$-      303
Metronidazole      306
Micellar fibers of surfactants      352—353
Micelles, globular (= spherical)      353
Micelles, polymeric (= covalent), dendritic      354—356
Michael-type additions, $a^{3}$ + alkyl d      20—21
Michael-type additions, $a^{3}+d^{0}$      274—275 291 316 351 354
Michael-type additions, $a^{3}+d^{1}$      65—66 75—76 205
Michael-type additions, $a^{3}+d^{2}$      71—74 205 318 339
Michael-type additions, $a^{3}+d^{2}$, reversibility      72
Michael-type additions, $a^{3}+d^{3}$ (Sakurai reaction)      90
Microbiological methods, literature      118
Microbiological methods, norgestrel synthesis      278
Mimoun’s complex      see “Molybdenum ...”
Mismatch oligonucleotide primer      245—246
Mitsunobu type reactions      160—161
MMTS      see “Methane (methylsulfinylXmethylthio)-”
Moffatt — Pfitzner or Swern oxidation of alcohols      133—134 323 325—327
Moffatt’s reagent      160 327—328
Molybdenum, (hexamethylphosphoric triamide-O)oxodiperoxy(pyridine)- (Mimoun’s complex, $\mathrm{[MoO(O_{2})_{2}(Hmpta)(Py)]}$), $\alpha$-hydroxylation of enolates      121—122
Molybdenum, (hexamethylphosphoric triamide-O)oxodiperoxy(pyridine)- (Mimoun’s complex, $\mathrm{[MoO(O_{2})_{2}(Hmpta)(Py)]}$), ox. cleavage of dialkylborinic esters      60—61
Monocyclic compounds      3 (see also “Carbocycles” “Heterocycles”)
Monodisperse dendritic polymers      355
Monosaccharides, $\omega$-deoxy-$\omega$-halo-, synthesis      266 269—270
Monosaccharides, $\omega$-deoxy-, by redn. of tosylates      114
Monosaccharides, glycosyl halides      266 268—272
Monosaccharides, glycosyl imidates      270—271
Monosaccharides, homologization with 1,3-dithiane      267
Monosaccharides, homologization with cyanide/DIBAL      50
Monosaccharides, homologization, stereoselective (Wittig/Sharpless)      264—265
Monosaccharides, protection and activation      157—161 266—273
Monosaccharides, table, pr.      263—264
Monosaccharides, thioglycosides      269 271
Monosaccharides, total synthesis      264—265
Monothioacetals      see “1
Monothioacetals, activation for substitution of sulfur      271
Monothioacetals, cyclic, prepn. from thionolactones      110—111
Monothioacetals, cyclic, reductive desulfurization      110—111
Monothioacetals, elimination of thiols      265
Monothioacetals, reductive desulfurization      273
Monothioacetals, S-alkyl O-trialkylsilyi, non-enolizable $a^{1}$-synthons      15—16
Monothioacetals, synthesis by Pummerer rearr.      51 265
Morphinane alkaloids by phenol coupling      294
Morpholine, enamines from      13—14 88
MPM = (4-methoxyphenyl)methyl, O-protective group      157 326—329
mRNA (messenger-RNA) for gene cloning      242
mRNA = messenger RNA, gene cloning      242
Mukaiyama aldol type reactions      58 62
Mukaiyama’s reagent      328—329
Mutagenesis, insertion of DNA      243—245
Mutagenesis, single-site mutations      245—246 341—343
myo-Inositol, selective glycosylation      270
N,N'-Dicyclohexylcarbodiimide      see “Carbodiimide”
N-, P- and S-Oxides, deoxygenation      115
N-Bromoacetamide      see “Acetamide N-bromo-”
N-Bromosuccinimide (= NBS)      see “2 1-bromo-”
N-Heteroarenes, reduction of      112—113 212 303 309
N-Heteroarenes, syntheses of      146—153
N-Heteroarenes, syntheses of, by oxn. of heterocycles      120—121 148 249
N-Heteroarenes, syntheses of, drugs      307—310
N-Heteroarenes, syntheses of, indoles      151—152 296 307
N-Heteroarenes, syntheses of, tautomerism      148
N-Heterocycles      146—154 (see also “Lactams”)
N-Heterocycles by redn. of lactams      111—112 247 291
N-Heterocycles, 5-membered, syntheses      148—153
N-Heterocycles, 5-membered, syntheses, ene reactions      297—298
N-Heterocycles, 5-membered, syntheses, Fischer’s indole synth.      151—152 296 307
N-Heterocycles, 5-membered, syntheses, intramol. reactions      34—35 291 305—309
N-Heterocycles, 5-membered, syntheses, Knorr’s pyrrole synthesis      150—151
N-Heterocycles, 5-membered, syntheses, sigmatropic rearr.      298—299
N-Heterocycles, 5-membered, syntheses, Wittig cyclization      32
N-Heterocycles, 5-membered, syntheses, [2+3]cycloadditions      35 49 51 152—153
N-Heterocycles, 6-membered, syntheses      148—149
N-Heterocycles, 6-membered, syntheses, electrocyclization      295—296
N-Heterocycles, 6-membered, syntheses, hetero[2+4]cycloaddn      153—154 297
N-Heterocycles, 6-membered, syntheses, intramol. $S_{E}$ of arenes      291—293
N-Heterocycles, 6-membered, syntheses, intramol. $S_{N}$ with nitrogen nucleophiles      291 294 304 306—308 310
N-Heterocycles, 6-membered, syntheses, redn. of pyridines      112—113 303 309
N-Heterocycles, 7-membered, by intramol. $S_{N}$      304 307
Naftifine      302
Naphthalene, 1,4,5,8-tetrahydro-, prepn.      104
Naphthalene, 1,4,5,8-tetrahydro-, selective epoxidation      124
Naphthalene, 4a,8a-dihydro-, cis-, photoisomers      332
Naphthalene, Birch redn. of      104
Naphthalene, naphthalene/K or Li, deprotonation with      52
Naphthalene, naphthalene/Na, red. deblocking with      220
NBA      see “Acetamide N-bromo-”
NBS      see “2 1-bromo-”
NCS      see “2 1-chloro-”
Nef reaction      16 65—66
Neighboring group participation in reactions of 2-O-acylglycosyl compounds      270—272
Nickel(0), $bis(\eta^{3}-alkenyl)$-, allyl coupling      42
Nickel(0), $bis(\eta^{3}-alkenyl)$-, trapping, with 1,2-propadiene      41
Nickel(0), $bis(\eta^{3}-alkenyl)$-, trapping, with isocyanides      41
Nickel(0), $di-mu-bromobis[(1,2,3-\eta)-3-methyl-2-butenyl]di$-, terpene synthesis with      42
Nickel(0), butadiene cyclooligomerizn. with      41
Nickel(0), tetracarbonyl-, allyl coupling with      42
Nickel(2+), catalyst for 2,3-reduction of 2-enones with $NaBH_{4}$      322—323
Nickel-aluminum alloy, activated      see “Raney nickel”
Nitrenes = imidogens by oxidation of amines with Pb(4+)      212—213
Nitrenes = imidogens from azides      147—148 154
Nitric acid, $N^{\underline{\omega}}$-nitro protection of arginine      229
Nitrile N-oxides      153
Nitrile N-ylides = N-alkylidyne aminium inner salts      153
Nitriles to aldehydes      50 112 298
Nitriles to aldehydes via carboximidic esters      22—23 298
Nitriles to aldehydes via carboximidic esters to amines      50 98
Nitriles to aldehydes, $\alpha$-spiroanellation      298 300
Nitriles to aldehydes, reductive cleavage (decyanidation)      280
Nitriles to aldehydes, synthesis from ketones with TosMIC      49
Nitriles, $\alpha$-alkylation      200 298 300 302—304
Nitriles, $\alpha$-hydroxy- (cyanohydrins)      18 50
Nitriles, addn. of carbanions to      201 299
Nitriles, addn. of enolate type anions to      58—59
Nitriles, addn. of N-nucleophiles to      305 308
Nitriles, conversion to carboximidic esters      22—23 298
Nitriles, conversion to carboxylic esters      300 304
Nitriles, conversion to cyclic amidines      305
Nitriles, Diels — Alder addition to      154
Nitriles, heterocycles from      298—299 307—308
Nitriles, hydrolysis to amides      66 302 303 304
Nitroalkanes, $d^{1}$-synthons      6 65—66 301 302
Nitroalkanes, carbon acidity      6
Nitroalkanes, conversion to carbonyl compds.      16 65—66
Nitroalkanes, reduction to amines      66 98 112 297 302
Nitroalkenes, $a^{2}$-synthons      16
Nitroalkenes, diene addition to      297
Nitroalkenes, redn. to ketones      301
Nitroalkenes, synthesis      301
Nitroarenes, reduction to arenamines      253
Nitroarenes, reductive N,N-coupling      305
Nitrofurantoin      308
Nitrones = N-alkylidene amine N-oxides      153
Nitrosyl chloride, diazotization with      312—313
Nitrosyl chloride, nitrite esters from      286
Nitrosyl chloride, nitrosation of enol ethers      268
Nocardicinic acid, 3-amino- (ANA), 1,1-dimethylethyl ester, synthesis      161
Nonanedioic acid, 5-hydroxy-2,4,6,8-tetramethyl-, diastereoselective lactonization      168 327—328
Norbornane etc.      see “Bicyclo[2.2.1]heptane” etc.
Norgestrel, $(\pm)$-, total synth.      278
Norphedrine = (R*,S*)-$\alpha$-(1-aminoethyl)benzenemethanol, $(+)-(\alpha S)$-, chiral auxiliary      61
Norphedrine = (R*,S*)-$\alpha$-(1-aminoethyl)benzenemethanol, $(\pm)$, synthesis      302
Noyori hydrogenation      102—103 325—326
Nucleophiles      see “Donor synthons”
Nucleotides, oligonucleotide syntheses      215—224 341—343
Nucleotides, protection      157—160 166—167 216—224
Octane, 2-iodo-, (R)-, stereosel. acylation      22
OEP      see “Porphine Octaethyl-”
Olefination      see “Alkenes”
Olefins      see “Alkenes”
Oleic acid      see “9-Octadecenoic acid (Z)-”
Oligocyclic compounds      90—94 329—339 356—357
Oligocyclic compounds, bridged      92—94 329—338
Oligocyclic compounds, bridged, special syntheses, alkaloids      291 293—294 296—298
Oligocyclic compounds, bridged, special syntheses, intramolecular aziridination, alkene + amine + $\mathrm{Pb(OAc)_{4}}$      212—213
Oligocyclic compounds, bridged, special syntheses, intramolecular aziridination, alkene + amine + $\mathrm{Pb(OAc)_{4}}$, intramolecular cyclopropanation      76 94
Oligocyclic compounds, bridged, special syntheses, intramolecular aziridination, alkene + amine + $\mathrm{Pb(OAc)_{4}}$, oxidative phenol coupling      293—294
Oligocyclic compounds, bridged, special syntheses, intramolecular aziridination, alkene + amine + $\mathrm{Pb(OAc)_{4}}$, photocyclizations      329—333
Oligocyclic compounds, bridged, special syntheses, intramolecular aziridination, alkene + amine + $\mathrm{Pb(OAc)_{4}}$, pinacol coupling      53
Oligocyclic compounds, bridged, special syntheses, intramolecular aziridination, alkene + amine + $\mathrm{Pb(OAc)_{4}}$, polar cyclizations      93 211—212 291 309 330 334
Oligocyclic compounds, bridged, special syntheses, intramolecular aziridination, porphyrins, bridged      253
Oligocyclic compounds, bridged, special syntheses, intramolecular aziridination, rearrangement, light-induced      329—333 337—338
Oligocyclic compounds, bridged, special syntheses, intramolecular aziridination, rearrangement, metal-catd. or thermal      79—80 332—336
Oligocyclic compounds, bridged, special syntheses, intramolecular aziridination, rearrangement, sulfur extrusion      38—39 338
Oligocyclic compounds, bridged, special syntheses, intramolecular aziridination, rearrangement, tetrapyrrole pigments      250—262
Oligocyclic compounds, bridged, special syntheses, intramolecular aziridination, rearrangement, Wittig reactions      333—334
Oligocyclic compounds, bridged, special syntheses, [2+2]cycloadditions      78 276 297—298 333 337
Oligocyclic compounds, bridged, special syntheses, [2+4]cvcloadditions      78 85—86 92—93 209—210 212 297 331 333—337
Oligocyclic compounds, fused, fragmentation      89—90 141—142
Oligocyclic compounds, fused, special syntheses, $6\pi$-electrocyclizations      38 295—296 338
Oligocyclic compounds, fused, special syntheses, alkaloids      289—298
Oligocyclic compounds, fused, special syntheses, carbonylation of cyclic boranes      48
Oligocyclic compounds, fused, special syntheses, cationic 1, 5-diene cyclizations      90—92 279—280
Oligocyclic compounds, fused, special syntheses, cyclopentanellations      58—59 81
Oligocyclic compounds, fused, special syntheses, Diels — Alder anellations      78 80—82 84—86 280—281 297
Oligocyclic compounds, fused, special syntheses, drugs      307—308 310
Oligocyclic compounds, fused, special syntheses, ene reactions      297—298
Oligocyclic compounds, fused, special syntheses, indoles      151—152 296 307
Oligocyclic compounds, fused, special syntheses, Robinson anellations      71—73 298
Oligocyclic compounds, fused, special syntheses, tetracyclines      318
Oligocyclic compounds, fused, special syntheses, Torgov cyclization      278—279
Oligocyclic compounds, fused, special syntheses, [2+2+2]cyclotrimerization of alkynes      80 281 330
Oligocyclic compounds, fused, special syntheses, [2+2]cydoaddition      78
Oligocyclic compounds, retro-synthetic analysis      3 208—209 210—213
Oligocyclic compounds, spirocyclic      see “Spiroanellation”
Oligocyclic hydrocarbon derivs., pr.      192
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