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Schiff's Base CH3CON=C(CH3)CH2CO2CH2CHSt CH3N=CHCH(CHg)2 CH3N=CHCH2CH(CHS)2 CH3N=CHCH=C(CH3) (CH2J2- CH=C(CH3)2f CH3N=CHC6H5 CH3N=CHC6H5 CH3N=CHC6H5 0-CH3N=CHC6H4CH3 P-CH3N=CHC6H4CH3 CH3N=CHCH2C6H5 CH3CH2N=CHCH3 CH3CH2N=CHCH2CH3I CH3CH2N=CH(CH2)2CH3t CH3CH2N=CHCH2CH(CH3)2f CH3CH2N=CHCH2CH(CH3)2f CH3CH2N=CHCH=C(CH3) (CH2)*- CH=C(CH3)2f CHsCH2N=CHCO2H CH3CH2N=C(CH3)CO2H CH3CH2N=C(CH3)CH2CO2CH2CHBt CH3CH2N=CHC6H5 CH3CH2N=CHC6H5t CHsCHsN^HCsHfit TABLE X—-Continued PREPARATION OF SECONDARY AMINES H. By Reduction of Schtff s Bases Derived from Aliphatic Amines—Continued Reducing Agent H2+Pt Na + CH3CH2OH Na + CH3CH2OH H2 + Pt H2 + Ni Electrolytic Pb cathode Na-Hg + CH3CH2OH H2 + Ni H2 + Ni Na + CH3CH2OH Electrolytic Pb cathode H2+Pt H2+Pt H2 + Ni H2+ Pt H2+Pt H2+ Pt H2+ Pt H2+ Pt H2 + Ni Na-Hg + CH3CH2OH H2+ Ni Product H2NCH(CH3)CH2CO2CH2CH3 CH3NHCH2CH(CH3)2 CH3NH(CH2)2CH(CH3)2 CH3NH(CH2)2CH(CH3) (CH2)3- CH(CH3)2 CH3NHCH2C6H5 CH3NHCH2C6H5 CH3NHCH2C6H5 0-CH3NHCH2C6H4CH3 P-CH3NHCH2C6H4CH3 CHsNHtCH^CeHs (CH3CHs)2NH CH3CH2NH(CHs)2CH3 CH3CH2NH(CH2) 3CH3 CH3CH2NH(CH2)2CH(CH3)2 CH3CH2NH(CH2)2CH(CH3)2 CH3CH2NHCH2CH[CH(CHS)2] (CH2)2- CH(CH3)S CH3CHSNH(CHS)2CH(CH3) (CH2)3- CH(CH3)S CH3CH2NHCHSCO2H CH3CH2NHCH(CH3)CO2H CH3CH2NHCH(CH3)CH2COSCHSCH3 CH3CH2NHCH2C6H5 CH3CH2NHCH2C6H5 CH3CH2NHCH2C6H5 Yield, % _ 59 46 Low Excellent — Excellent Excellent — 43 33 — 20 16 55 30 — Excellent 70 — Ref.* 62 157 157 20 119 158 159 119 119 160 158 55 55 63 58 20 62 62 62 119 159 63 to CO O H-i O & > O H i—i O GQ
CH3CH2N=CHC6H5J CH3(CH2)2N=CHCH3f CH3(CH2)2N==CH(CH2)2CH3f CH3(CH2)2N=CHCH(CH3)2t CH3(CH2)2N==CHCH2CH(CH3)2t CH3(CH2)2N=CHC6H5 CH3(CH2)2N=CHC6H5t (CH3)2CHN=CH(CH2)2CH3f CH3(CH2)3N=CH2 CH3(CH2)3N=CHCH3f CH3(CH2)3N=CHCH3 CH3(CH2)3N=CHCH2CH3t CH3(CH2)3N=CHCH2CH3 CH3(CH2)3N=CHCH(CH3)2 CH3(CH2)3N=CH(CH2)3CH3 CH3(CH2)3N=CHCH2CH(CH3)2t CH3(CH2)3N=CHCH2CH(CH3)2 CH3(CH2)3N=CHC6H5 (CH3)2CHCH2N=CHC6H5f (CH3)2CH(CH2)2N=CHCH=C(CH3)- (CH2)2CH==C(CH3)2f (CH3)2CH(CH2)2N=C(CH3)CH2C02- CH2CH3 f C5H11N=CHC6HSf C6H13N=CHC6HSf CH3CH2C(CH3)=CHN=CHCH(CH3)- CH2CH31 * H2 + Ni H2 +Pt H2+Pt H2+Pt H2+Pt H2 + Ni Na-Hg + CH3CH2OH H2+Pt H2 + Ni H2+Pt H2 + Ni H2+Pt H2 + Ni H2 + Ni H2 + Ni H2+ Pt H2 + Ni H2 + Ni Na-Hg + CH3CH2OH H2+Pt H2+Pt Na-Hg + CH3CH2OH H2+Pt H2 + Ni * References 134-180 are listed on p. 255. t These Sehiff's bases probably were purified before reduction. ! CH3CH2NHCH2C6H5 C6H5CH3 CH3CH2NH2 NH3 (CH3CH2)2NH (CH3CH2)3N CH3(CHa)2NHCH2CH8 CH3(CH2)2NH(CH2)3CH3 CH3(CH2)2NHCH2CH(CH3)2 CH3(CH2)2NH(CH2)2CH(CH3)2 CH3(CHz)2NHCH2C6H6 CH3(CH2)2NHCH2C6H5 I (CHS)2CHNH(CH2)SCH3 j CH3(CH2)3NHCH3 I CH3(CH2)3NHCH2CH3 I CH3(CH2)3NHCH2CH3 CH3(CH2)aNH(CH2)2CH3 CH3(CH2)3NH(CH2)2CH3 CH3(CH2)sNHCH2CH(CHs)2 I CH3(CH2)3NH(CH2)4CH3 I CH3(CH2)sNH(CH2)2CH(CH8)2 ! CH3(CH2)3NH(CH2)2CH(CH3)2 i CH3(CH2)3NHCH2C6H5 (CHa)2CHCH2NHCH2C6H5 (CH3)2CH(CH2)2NH(CH2)2CH(CH3)- (CH2)3CH(CH3)2 (CH3)2CH(CH2)2NHCH(CH3)CH2C02- CH2CH3 C5H1INHCH2C6H5 C6H13NHCH2C6H5 CH3CH2CH(CH3)CH2NHCH2CH(CH3)- CH2CH3 Mostly 40 45 63 47 Excellent — 44 26 52 31 54 31 56 51 58 41 Excellent — 50 — Almost quantitative 83 161 55 55 55 55 119 159 55 79 55 79 55 79 79 79 55 79 119 159 20 62 159 118 162 !> > H H-I O tzj O > I—S OQ d d o < % H-i O 3 OO OS
Page 1 and 2:
Organic Reactions VOLUME IV EDITORI
Page 3 and 4:
PREFACE TO THE SERIES In the course
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CONTENTS CHAPTER PAGE 1. THE DIELS-
Page 7 and 8:
CHAPTER 1 THE DIELS-ALDER REACTION
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2. C6H5CH=CHA. DIENE SYNTHESIS I S
Page 11 and 12:
DIENE SYNTHESIS I 5 ^Lehmann, Ber.,
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DIENE SYNTHESIS I 7 and IV for thes
Page 15 and 16:
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
Page 31 and 32:
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
Page 37 and 38:
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
Page 159 and 160:
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
Page 183 and 184:
Page 185 and 186:
Page 187 and 188: PREPARATION OF AMINES BY REDUCTIVE
Page 215 and 216: CH3CH=CHCHO CH3(CHS)2CH=C(CH2CH3)CH
Page 217 and 218: (CHs)2C=CHCOCH3 (CH3)2C=CH(CH2)2COC
Page 219 and 220: CH3COCH3 CH3COCH3 CH3COCH2CH3 CH3CO
Page 221 and 222: H2N (CH2) 2NH2 H2N(CH2)2NH2 H2N{CH2
Page 223 and 224: P-HOC6H4CH2CH(CH3)NH2 CH2O P-CH3OC6
Page 225 and 226: CH3NH2 CH3NH2 CH3NH2 CH3NH2 CH3NH2
Page 227 and 228: HO(CH2)2NH2 HO(CHa)2NH2 HO(CH2)2NH2
Page 229 and 230: (GHg)2COHCH2NH2 (CHs)2COHCH2NH2 CH3
Page 231 and 232: Amine, Nitro, Nitroso, or Azo Compo
Page 233 and 234: P-HOC6H4NH2 P-HOC6H4NH2 - P-HOC6H4N
Page 235 and 236: CeHgNHs C6H5NH2 C6HgNH2 C6H5NH2 P-C
Page 237: HN=C(CH3)CO2H CH2 SehifPs Base / \
Page 241 and 242: C6HuN=CH(CH2)2CH3t C6Hi1N=CH(CH2)2C
Page 243 and 244: p-C6H5(CH2)2N=CHC6H40H f p-C6H5(CH2
Page 245 and 246: C6H5N-=CHCH2CH(CH3)2f C6H5N=CH(CHOH
Page 247 and 248: 2,4'-CH3C6H4N=CHC6H4CIf 2,4 / -CH3C
Page 249 and 250: 0-CH3OC6H4N=CH(CHOH)4CH2OH m-CH3OC6
Page 251 and 252: Amine Used CH3CH2NH2 Amine Used CH3
Page 253 and 254: Nitro Compound Used ^HOC6H4NO2 P-H2
Page 255 and 256: C6H5CHOHCH2CH(CH3)- NHCH3 C6H5CHOHC
Page 257 and 258: Amine Used (CHs)2NH (CHs)2NH (CH3)2
Page 259 and 260: C6H5NH(CHs)2CH3 C6H5NH(CHs)3CH3 C6H
Page 263 and 264: THE ACYLOINS 257 euphony and to avo
Page 265 and 266: THE ACYLOINS 259 A mechanism simila
Page 267 and 268: THE ACYLOINS 261 There is a strikin
Page 269 and 270: TSE ACYLOINS 263 upon the rigid exc
Page 271 and 272: THE ACYLOINS 265 carbonate. This pr
Page 273 and 274: THE ACYLOINS 267 is thought that py
Page 275 and 276: CHAPTER 6 THE SYNTHESIS OF BENZOINS
Page 277 and 278: THE SYNTHESIS OF BENZOINS 271 are i
Page 279 and 280: THE SYNTHESIS OF BENZOINS 273 metri
Page 281 and 282: THE SYNTHESIS OF BENZOINS 275 Symme
Page 283 and 284: THE SYNTHESIS OF BENZOINS 277 cent
Page 285 and 286: THE SYNTHESIS OF BENZOINS 279 Since
Page 287 and 288: 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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Page 325 and 326:
Page 327 and 328:
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Page 331 and 332:
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SYNTHESIS OF BENZOQUINpNES BY OXIDA
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Page 343 and 344:
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Page 347 and 348:
Page 349 and 350:
Page 351 and 352:
Quinone 5,6-Dimethoxy-2hydi oxyquin
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Quinone 3-Hydroxythymoqui- J none |
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Quinone 2-Methoxy-6-tridecylquinone
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Page 359 and 360:
Page 361 and 362:
Page 363 and 364:
Page 365 and 366:
Page 367 and 368:
Page 369 and 370:
ROSENMUND REDUCTION 363 For accompl
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ROSENMUND REDUCTION 365 acid in alm
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ROSENMUND REDUCTION 367 The Hydroge
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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
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THE WOLFF-KISHNER REDUCTION 383 dan
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THE WOLFF-KISHNER REDUCTION 385 Sod
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THE WOLFF-KISHNER REDUCTION 387 TAB
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THE WOLFF-KISHNER REDUCTION 389 Red
Page 397 and 398:
THE WOLFF-KISHNER REDUCTION 391 Dir
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C7Hi2O C7H14O C7H0O2 C7H8O2 C7H6O4
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C9Hi0O C9Hi2O C9Hi4O Formula C9Hi6O
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Formula Ci0Hi6O CioHisO Ci0H6O2 Ci0
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Formula CnH16O CnHi8O CnHi6O2 CnHi8
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Formula Ci3H22O C13H10O3 Ci3Hi8O3 C
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Formula CI6HHO2 CI6HHO3 CI6H24O3 C1
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Formula Ci8H13ON Ci8H2IO3N Ci8Hi9O4
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Formula C2IH34O C21H30O2 C21H32O2 C
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Formula C23H32O7 C23Hi7ON C24H3603
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Formula C25H40O7 C26Hi6O C26H44O C2
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Formula C29H46O C29H46O2 C29H48O3 C
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Formula C32H52O3 C32H46O4 C32H50O4
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THE WOLFF-KISHNER REDUCTION 417 133
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DEX Numbers in bold-face type r :ef
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Dialkylaminoquinonedisulfonates, 35
Page 433 and 434:
3-Methylpyrene, preparation by Wolf
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