Organic Reactions Volume 4 - Sciencemadness Dot Org

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402 ORGANIC REACTIONS Formula Ci5H8O Ci5Hi0O Ci5Hi2O C15H14O Ci6Hi8O Ci6H22O Ci5H28O Ci5Hi0O2 Ci5Hi4O2 Ci6H20O2 Ci6Hi4O8 Ci6H28ON Ci6Hi2O Ci6Hi4O Ci6H20O Ci6H24O Ci6Hi2O2 TABLE II—Continued COMPOUNDS REDUCED BY THE WOLFF-KISHNER METHOD Compound l-Perinaphthindenone 9~Anthraldehyde 9-Anthraldchyde 9-Phonanthraldehyde Benzalacetophenone 3 (2'-Naphthyl)-cyclopenten-2one»l Dibenzyl ketone 9-Keto~12-methyM,2,3,4,9,10, 11,12-octahy drophenanthrene1-Keto-ll-methyloctahydrophenanthrene Gurgunene ketone Cedrone a-Gyporone a-Vetivone /3-Vetivone j9~Vetivone Ketones from Zingiber root p-Tolyl w-heptyl ketone p-Tolyl n-hcptyl ketone Cyclopentadecanone a-Benzoylcoumarone 6-Methoxy-l-keto~l,2,3,4tetrahydrophenanthrene 2-Keto-4«fur y 1- 10-methyldecalin Di-p-anisyl ketone 4-Methyl-3-aminophenyl n-heptyl ketone 9-Methyl-10-anthraldehydo 1-Acetylanthracene 2-Acetylanthracene 2-Methyl-3~phenylindone l-Keto-l,2,3,44etrahydro-8,9acephenanthrene 4-Phenylcamphor 9-Phenyl-3~decalone p-Tolyl w-octyl ketone Perisuccinoylacenaphthene CI5 Product Normal Normal Normal Normal 1,2-DiphenylcycIopropane Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Ci6 Normal Normal § Normal Normal Normal Normal Normal Normal Normal Method K WH K WS KP WS WII WS WS WS WS WS WSf WSf WS I WS WD WD, WS WS WH WS WS WKI WD WH WS WD WH WD WH K WD WD Yield 19B 38B 79B __ — 49B 82B — __ 29B — 42B 5OB 44B 81B _ 62B — 5OB _ 74B 100B Good 10OB Poor 85B 7OA —• ~ Reference* 231 232 20 232a 233 234 2 235 236 237 238 239 240 240 241 242 129 130 24 54 242a 243 26 130 216 9 9 244 245 246 246a 129 78 * References 86a-413 are listed on pp. 416-422. t The semicarbazone was added to aqueous potassium hydroxide containing a little copper sulfate and the solution heated slowly in vacuum until both the water and the product had distilled. % No alkaline catalyst was used. § The reaction proceeded normally when the semicarbazone was reduced for four hours at 180° when the ketone was reduced directly at 180° for eight hours, 2-ethylanthracene was formed.
Formula CI6HHO2 CI6HHO3 CI6H24O3 C16H30O3 Ci6H14O4 Ci6H9ON Ci6Hi3ON Ci6H8ONCl C17H10O Cl7Hl2O Ci7Hi4O Ci7Hi8O C17H30O Ci7H32O CnH10O2 Ci7Hi2O2 Ci7H16O3 Ci7H26O3 THE WOLFF-KISHNER REDUCTION 403 TABLE II—Continued COMPOUNDS REDUCED BY THE WOLFF-KISHNER METHOD Compound 3-(6'-Methoxy-2'-naphthyl)cyclopenten-2-one-l /S-(3~Acenaphthoyl)-propionic acid 3,5-Dimethoxyphenyl w-heptyl ketone Mixture of methyl 2-ethyI- 2-butyl-5~ketonononoate and methyl 4-ethyl-4-butyl- 5-ketonononoate /3-(p-Phenoxybenzoyl)-propionic acid 1,2-Benzo~3-azafluorenone 2,3-Benzo-l-azafluorenone 3,4-Benzo-2-azafluorenone 3-Acetyl-2-phenylpyrrocoline 4-Chlor o-l ,2-benzo-3-azafluorenone Pyrene-3-aldehyde Pyrene-3-aldehyde a-Benzoylnaphthalene /3-Benzoylnaphthalene /8-Propionylanthracene Dibenzalacetone 3-Keto-l,2,3,9,10,ll-hexahydro-1,2-cyclopentenophenanthrene3-Keto-l,2,3,9,10,ll-hexahydro~l,2~cyclopentenophenanthrene l-Methyl-4-keto-l,2,3,4-tetra~ hydro-7-ethylphenanthrene Civetone Dihydrocivetone 2-Methylaceanthrenequinone ?-Methylaceanthrenequinono p-Hydroxyphenyl /3-naphthyl ketone 3-(2-Naphthyl)cyclopentanl-one-2-acetic acid 3,5-Dimethoxyphenyl n-octyl ketone Normal Normal Normal Product Mixture of normally reduced acids Normal Normal Normal Normal Normal J 4-Hydroxy-l,2-benzo-3-azafluorene Ci7 Normal Normal Normal Normal , Normal § Normal Normal Normal Normal || Normal None None Normal Normal Normal Method WS WD ? WH WD WDt WDt WDt WD WDt WD K WDt WDt WD K ? WS ? WS WS ? ? WDt WS ? Yield 37B 99A (cr.) — 95A (cr.) _ 8OA — 35A 85A 9OA 84B 55A 96A Good — Reference* * References 86o-413 are listed on pp. 416-422. f No alkaline catalyst was used. J There was also formed 45% of 2-phenylpyrrocoline. § With one mole of hydrazine there was formed the pyrazoline which on warming was converted to 3,4-diphenylcyclopentene. When the ketone was treated with excess hydrazine there was formed a dimeric product, converted by the action of potassium hydroxide into l-phenyl-2-(|8-phenylethyl) cyclopropane. U There was also formed 31% of civetol, — 65B — — 79A 85A 234 40 247 247a 40 86 86 248 249 28 27 20 29 29 9 250 71 250a 251 252 24 253 253 29 253a 254
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Organic Reactions VOLUME IV EDITORI
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PREFACE TO THE SERIES In the course
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CONTENTS CHAPTER PAGE 1. THE DIELS-
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CHAPTER 1 THE DIELS-ALDER REACTION
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2. C6H5CH=CHA. DIENE SYNTHESIS I S
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DIENE SYNTHESIS I 5 ^Lehmann, Ber.,
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DIENE SYNTHESIS I 7 and IV for thes
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DIENE SYNTHESIS I 9 tion of the com
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Maleic anhydride Fumaric anhydride
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DIENE SYNTHESIS I 13 jugated system
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DIENE SYNTHESIS I 15 Mesaconic (met
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DIENE SYNTHESIS I 17 An interesting
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DIENE SYNTHESIS I 19 CH2 CH3 O Il I
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CH C2H5 I CH2 XXX DIENE SYNTHESIS I
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DIENE SYNTHESIS I cyclic dienes fre
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DIENE SYNTHESIS I 25 Although l,2,3
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DIENE SYNTHESIS I 27 Certain types
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DIENE SYNTHESIS I 29 Hydrocarbons c
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DIENE SYNTHESIS I 31 Diels-Alder re
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DIENE SYNTHESIS I 33 give LXXX. If
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DIENE SYNTHESIS I 35 Numerous other
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DIENE SYNTHESIS I 37 Maleic anhydri
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DIENE SYNTHESIS I 39 Indole derivat
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DIENE SYNTHESIS I 41 anhydride. In
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DIENE SYNTHESIS I 43 tetrahydronaph
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DIENE SYNTHESIS I 45 TABLE III—Co
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DIENE SYNTHESIS I 47 TABLE IV ADDtr
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Cycloheptatriene DIENE SYNTHESIS I
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BIENE SYNTHESIS I 51 TABLE V—Cont
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DIENE SYNTHESIS I 53 TABLE VI ADDTJ
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BIENE SYNTHESIS I 55 TABLE VII—Co
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DIENE SYNTHESIS I 57 REFERENCES TO
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DIENE SYNTHESIS I 59 422 Diels and
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DIENE SYNTHESIS II 61 PAGE TABLKs O
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DIENE SYNTHESIS II 63 The configura
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DIENE SYNTHESIS II 65 Aromatic comp
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DIENE SYNTHESIS II 67 55%). 13 Cycl
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H8Cr H8C JCO2H XSV iOCH, DIENE SYNT
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DIENE SYNTHESIS II 71 additions wit
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DIENE SYNTHESIS II , 73 been report
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DIENE SYNTHESIS II 75 drogenation u
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DIENE SYNTHESIS II 77 Allyl, Vinyl,
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DIENE SYNTHESIS II 79 (XLVII) that
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~r (PH.)* + CO2H CO5 :H CO2CH3 CO2C
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DIENE SYNTHESIS II 83 covered as th
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DIENE SYNTHESIS II 85 anhydride fro
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DIENE SYNTHESIS II 87 or even preve
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DIENE SYNTHESIS II 89 SELECTION OF
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DIENE SYNTHESIS II 91 liquid separa
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Acetylenic Dienophile Ethyl acetyle
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DIENE SYNTHESIS II 95 TABLE IV YIEL
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1-Diethylaminobutadiene 1,1-Dimeth
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1-Methylbutadiene (piperylene) l-Me
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1,5,5,6-Tetramethylcyclohexadiene (
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1-Methyl-l-phenylbtrfcadiene l-Met
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Benzalacetophenone Bicyclohexenyl r
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f$-Benzoylacrylic acid, 2, b-dimeth
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Bicyelohexenyl c r 2,3-Dimethylbuta
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Isoprene Cinnamic acid,2,6~ dimetho
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Isoprene Cinnamic acid,omeihoxy- (t
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Coumann Butadiene 2,3-Dimethylbutad
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1,3-Dimethylbutadiene 1,4-Dimethyl
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1,1,3-Trimethylbutadiene 1,1,4-Tri
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2,3-Dimethylbutadiene Croio7toladon
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2,3-Dimethylbutadiene2,3-Diphenylbu
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Cyclopentadiene 2,3-Dimethylbutadie
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Z}4rDihydro-5-bromo- 1\8-dimethoxy-
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Z^Dihydro-l-ftieihoxy-2-naphthoic a
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Ethyl ethytidenemalonate Butadiene
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1,4-Diphenylbutadiene2,3-Diphenylbu
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6 The product gradually decomposes
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Cyclohexadiene Cyclopentadiene 2,3-
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p-Nitrostyrenej 3,4-cfomethoxy- 2,3
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Dihydrothiophene-1 - dioxide Butadi
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Piperylcyclone Tetraphenyleyelopent
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AUyI iodide Cyclopentadiene AUyI is
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Tetraphenylcyclopentadienone Pheney
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Indene a,a , -Diphenyl-/3,j3'isoben
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1,5,5-Trimethyleyclopentadiene Tri
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Addends Acetylene Tetraphenylcyelop
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Trimethylcyclopentadiene? (Damsky)
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Cyclopentadiene 9,10-Dibromoaiithra
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Propargyl aldehyde 2,3-Dimethylbuta
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Addends Acetylenedicarboxylic acid
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I-* SO N-ce-Dimethylindole 3,5-Dim
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Oi N-Methylindole a-Methylpyrrole N
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OS Quinaldine Quinoline CX | JCH. j
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2,3,4-Trimethylpyrrole H3Cp CCO2CH3
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1,3-Dimethylbutadiene 1,1,3-Trimet
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DIENE SYNTHESIS II 110 Diels and Al
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PREPARATION OF AMINES BY REDUCTIVE
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CH3CH=CHCHO CH3(CHS)2CH=C(CH2CH3)CH
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(CHs)2C=CHCOCH3 (CH3)2C=CH(CH2)2COC
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CH3COCH3 CH3COCH3 CH3COCH2CH3 CH3CO
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H2N (CH2) 2NH2 H2N(CH2)2NH2 H2N{CH2
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P-HOC6H4CH2CH(CH3)NH2 CH2O P-CH3OC6
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CH3NH2 CH3NH2 CH3NH2 CH3NH2 CH3NH2
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HO(CH2)2NH2 HO(CHa)2NH2 HO(CH2)2NH2
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(GHg)2COHCH2NH2 (CHs)2COHCH2NH2 CH3
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Amine, Nitro, Nitroso, or Azo Compo
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P-HOC6H4NH2 P-HOC6H4NH2 - P-HOC6H4N
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CeHgNHs C6H5NH2 C6HgNH2 C6H5NH2 P-C
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HN=C(CH3)CO2H CH2 SehifPs Base / \
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CH3CH2N=CHC6H5J CH3(CH2)2N=CHCH3f C
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C6HuN=CH(CH2)2CH3t C6Hi1N=CH(CH2)2C
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p-C6H5(CH2)2N=CHC6H40H f p-C6H5(CH2
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C6H5N-=CHCH2CH(CH3)2f C6H5N=CH(CHOH
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2,4'-CH3C6H4N=CHC6H4CIf 2,4 / -CH3C
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0-CH3OC6H4N=CH(CHOH)4CH2OH m-CH3OC6
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Amine Used CH3CH2NH2 Amine Used CH3
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Nitro Compound Used ^HOC6H4NO2 P-H2
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C6H5CHOHCH2CH(CH3)- NHCH3 C6H5CHOHC
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Amine Used (CHs)2NH (CHs)2NH (CH3)2
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C6H5NH(CHs)2CH3 C6H5NH(CHs)3CH3 C6H
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THE ACYLOINS 257 euphony and to avo
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THE ACYLOINS 259 A mechanism simila
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THE ACYLOINS 261 There is a strikin
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TSE ACYLOINS 263 upon the rigid exc
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THE ACYLOINS 265 carbonate. This pr
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THE ACYLOINS 267 is thought that py
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CHAPTER 6 THE SYNTHESIS OF BENZOINS
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THE SYNTHESIS OF BENZOINS 271 are i
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THE SYNTHESIS OF BENZOINS 273 metri
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THE SYNTHESIS OF BENZOINS 275 Symme
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THE SYNTHESIS OF BENZOINS 277 cent
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THE SYNTHESIS OF BENZOINS 279 Since
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Benzoin Reaction 1 * 54 Benzoin Ben
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LESS STABLE V C6H5COCHOHC6H4OCH3^ V
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THE SYNTHESIS OF BENZOINS 285 66-86
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THE SYNTHESIS OF BENZOINS 287 Aliph
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THE SYNTHESIS OF BENZOINS 289 the i
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THE SYNTHESIS OF BENZOINS 291 The e
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THE SYNTHESIS OF BENZOINS 293 effec
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THE SYNTHESIS OF BENZOINS 295 The e
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THE SYNTHESIS OF BENZOINS 297 ethox
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THE SYNTHESIS OF BENZOINS 299 C6HBC
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Formula CI5HHO2 CI6HHO3 CI6HHO3 CI5
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Formula C19H22O2 C20H1GO2 C20H24O2
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CHAPTER 6 SYNTHESIS OF BENZOQUINONE
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SYNTHESIS OF BENZOQUINONES BY OXIDA
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SYNTHESIS OF BENZOQUINpNES BY OXIDA
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Quinone 5,6-Dimethoxy-2hydi oxyquin
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Quinone 3-Hydroxythymoqui- J none |
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Quinone 2-Methoxy-6-tridecylquinone
Page 357 and 358: SYNTHESIS OF BENZOQUINONES BY OXIDA
Page 369 and 370: ROSENMUND REDUCTION 363 For accompl
Page 371 and 372: ROSENMUND REDUCTION 365 acid in alm
Page 373 and 374: ROSENMUND REDUCTION 367 The Hydroge
Page 375 and 376: ROSENMUND REDUCTION 369 solution of
Page 377 and 378: ROSENMUND REDUCTION 371 TABLE I ALI
Page 379 and 380: Acid Chloride Benzoyl chloride p-Ca
Page 381 and 382: Acid Chloride 3-Furoic- 4~Carbometh
Page 383 and 384: ROSENMUND REDUCTION 377 106 Shoesmi
Page 385 and 386: THE WOLFF-KISHNER REDUCTION 379 INT
Page 387 and 388: THE W0LFF-KISHNER REDUCTION 381 mol
Page 389 and 390: THE WOLFF-KISHNER REDUCTION 383 dan
Page 391 and 392: THE WOLFF-KISHNER REDUCTION 385 Sod
Page 393 and 394: THE WOLFF-KISHNER REDUCTION 387 TAB
Page 395 and 396: THE WOLFF-KISHNER REDUCTION 389 Red
Page 397 and 398: THE WOLFF-KISHNER REDUCTION 391 Dir
Page 399 and 400: C7Hi2O C7H14O C7H0O2 C7H8O2 C7H6O4
Page 401 and 402: C9Hi0O C9Hi2O C9Hi4O Formula C9Hi6O
Page 403 and 404: Formula Ci0Hi6O CioHisO Ci0H6O2 Ci0
Page 405 and 406: Formula CnH16O CnHi8O CnHi6O2 CnHi8
Page 407: Formula Ci3H22O C13H10O3 Ci3Hi8O3 C
Page 411 and 412: Formula Ci8H13ON Ci8H2IO3N Ci8Hi9O4
Page 413 and 414: Formula C2IH34O C21H30O2 C21H32O2 C
Page 415 and 416: Formula C23H32O7 C23Hi7ON C24H3603
Page 417 and 418: Formula C25H40O7 C26Hi6O C26H44O C2
Page 419 and 420: Formula C29H46O C29H46O2 C29H48O3 C
Page 421 and 422: Formula C32H52O3 C32H46O4 C32H50O4
Page 423 and 424: THE WOLFF-KISHNER REDUCTION 417 133
Page 429 and 430: DEX Numbers in bold-face type r :ef
Page 431 and 432: Dialkylaminoquinonedisulfonates, 35
Page 433 and 434: 3-Methylpyrene, preparation by Wolf
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