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334 ORGANIC REACTIONS TABLE II*—Continued ALKYL AND ARYL QUINONES AND THEIR SUBSTITUTED DERIVATIVES Quinone 3,6-Dichlorotoluquinone 5,6-Dichlorotoluqui- J f none Trichlorotoluquinone i Tetrachlorotoluquinone 5-Bromotoluquinone \ 6-Bromotoluquinone I 5~Bromo~3-chlorotoluquinone 5-Bromo-6~chlorotolu~ quinone G~Bromo-5~chlorotoluquinone 5-Br omo-3,6-dichlor otoluquinone 3,5-Dibromotoluqui- J none | 3,5-Dibromo-6-chlorotoluquinone 1_ Substance Oxidized 3,6-Dichlorotoluhydroquinone t 5,6-Dichlorotoluhydroquinone t 5,6-DichIor o-4-aminoo-cresolTrichlorotoluhydroquinono Crude o- and w-crcsolsulfonic acids o-Toluidine 3,5,6-Trichloro-4-aminoo-toluidine 3-Methylsulfanilic acid o-Cresol m-Cresol 4,6-Dichloro-o-crosol 2,4,6-Trichloro-w-cresol Beechwood creosote 5-Bromotoluhydroquinone5-Bromo-4-hydroxy-otoluidine5-Bromo~4~ammo~0cresol 4,6-Dibromo-o-cre8ol 6-Bromo-4-arnino-ocresol 6-Bromo~o-cresol-4sulfonic acid 5-Bromo-3-chloro~4hydroxy-o-toluidine 5-Bromo-6-chlorotolu~ hydroquinone t 6~Bromo-5-chlorotoluhydroquinone t 5-Brorno-3,6-dichloro~ tol uhydr oquinone 2,4,6-Tribromo-m-cresol 3,5-Dibromo-4~hydroxyo-toluidine 2,6-Dibromo-ra-cresol- 4»sulfonic acid 3,5-Dibromo~4,6~dichloro-o-cresol Oxidizing Agent Na2Cr2O7 (H2SO4) Na2Cr2O7 (H2SO4) — KClO8, HCl Na2Cr2O7, HCl Chromic acid KClO8, HCl KClC)8, HCl Cl2 (sunlight) Aqua rogia Aqua rogia KClO8, HCl FoCl8 or K2Cr2O7 (H2SO4) MnO2 (H2SO4) FeCl3 MnO2 (H2SO4) FeCl3 Na2Cr2O7 (AcOH) CrO8 (dil. AcOH) Na2Cr2O7 (H2SO4) CrO8 Na2Cr2O7 (H2SO4) K2Cr2O7 (H2SO4) K2Cr2O7 (H2SO4) HNO8 (AcOH) CrO3 (70% AcOH) Na2Cr2O7 (H2SO4) FeCl3 CrO3 (H2SO4) Fuming HNO8 — — —, —, Yield 38-40% —' — —, _ 16% 25% — —> 80% ± 80% ± —* Z _ —' 97% -_ — —, 77% —, Good Nearly quant. — * See p. 315 for explanation of system and abbreviations in tables. t References 152-247 are listed on pp. 336-338. j For a discussion of the probable structure of this hydroquinone, see p. 322. Eeferencesf 124 122, 124 125 223 182 225 227 148 226 228 229 229 230 122, 231 90 86 90 86 222 23 68 23 123 122 122 68 22, 26 (y.), 133 87 22 232 233
SYNTHESIS OF BENZOQUINONES BY OXIDATION 335 TABLE II—Continued ALKYL AND ARYL QUINONES AND THEIR SUBSTITUTED DERIVATIVES Quinone Tribromotoluquinone \ Tetrabromotoluquinone Pentabromotoluquinone 5 -lodotoluquinone 6-Iodotoluquinone 6~Iodo~3,5~dibromotoluquinone 3,5-Diiodotoluquinone 3-Nitrotoluquinone 3-Nitro-5- (or 6-)chlorotoluquinone 3- (or 5-)Nitro-5- (or 3-) chlorotoluquinone 3-(or5-)Nitro-5-(or3-)j bromotoluquinone | 3-(or5-)Nitro-5(or3),6~ dibromotoluquinone Triphenylquinone o-Xyloquinone (2,3-dimethylqui- j none) Dichloro-o-xyloquinone r Substance Oxidized 3,5,6-Tribr omo-4-chlor oo-cresol Tetrabromo-o-cresol 3,5,6-Tribromo-4~aminoo-cresol 2~Methyl-3,5,6-tribromo- 4*hydroxybenzyl alcoliol (and diacetate) 2-Methyl-3,5,6-tribromo- 4*hydroxybenzaldehyde Tetrabromo-ra-cresol Tribromotoluhydroqui- 2-Hydroxy-p-toluic acid 2-Hydroxy-5-niti op-toluic acid 2,4-6ts(Acetoxymethyl)- 3,(5,6-tribromopb.enol l-Dibromomothyl-3,5,6tribromo-4-hydioxybenzaldehyde 5-Iodo-4-amino-o~ci csol 5-Iodo-4-hydroxy-o toluidino 6- lodo-o-cr esol-4-sulf onic acid 4,6*Diiodo-3,5~dibromo~ o-cresol 2,6-Diiodo-m-cr esol- 4*sulforiic acid ! 3-Nitro-4-hydroxy-o- toluidine3-Nitro-4-hydroxy-0ioluidine 2~Chloro-:p-cresol 6-Nitro-2-chloro-2)-cresol 2-Bromo-p-cresol 6-Nitro-2-bromo-pqresol 6-Nitro-2,3- or 5-dibromo-p-cresol Triphenylhydroquinone nc-o-Xylidin 4-Hydroxy-tnc-o-xylidin 2,3-Dichloro-5,6-dimethyl-p-phenylenediamine * References 152-247 are listed on pp. 336-338. Oxidizing Agent Fuming HNO 3 Fuming HNO3 FeCl3 HNO3 HNO3 (sp. gr. 1.4) HNO3 (sp. gr. 1.4) HNO3 Br2 (AcOH) Br2 (AcOH) HNO3 HNO3 MnO2 (H2SO4) MnO2 (H2SO4) CrO3 (H2SO4) Fuming HNO3 Chromic acid PbO2 (H2SO4) Ca(OCl)2, HCl HNO3 (sp. gr. 1.5) HNO3 (sp. gr. 1.5) HNO3 (sp. Ki. 1.5) HNO3 (sp. gr. 1.5) HNO3 (sp. gr. 1.5) CrO3 (AcOH) MnO2 (H2SO4) Na2Cr2O7 (H2SO4) Fe2(SO4) 3 MnO2 (H2SO4) CrO3 (AcOH) — — — — — — — — — Yield 80% ± 80% ± 20% _ 15% — __ — J — — 66% 33% 61% 54% References* 233 133, 234 234 235 236 236 79 218 218 237 236 90 90 143, 144 (y.) 233 144 238 238 35 35 36 36 36 238a 239 75 (y.),240 85, 240a 240a 96
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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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Page 191 and 192:
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Page 195 and 196:
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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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Page 263 and 264:
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
Page 289 and 290: LESS STABLE V C6H5COCHOHC6H4OCH3^ V
Page 291 and 292: THE SYNTHESIS OF BENZOINS 285 66-86
Page 293 and 294: THE SYNTHESIS OF BENZOINS 287 Aliph
Page 295 and 296: THE SYNTHESIS OF BENZOINS 289 the i
Page 297 and 298: THE SYNTHESIS OF BENZOINS 291 The e
Page 299 and 300: THE SYNTHESIS OF BENZOINS 293 effec
Page 301 and 302: THE SYNTHESIS OF BENZOINS 295 The e
Page 303 and 304: THE SYNTHESIS OF BENZOINS 297 ethox
Page 305 and 306: THE SYNTHESIS OF BENZOINS 299 C6HBC
Page 307 and 308: Formula CI5HHO2 CI6HHO3 CI6HHO3 CI5
Page 309 and 310: Formula C19H22O2 C20H1GO2 C20H24O2
Page 311 and 312: CHAPTER 6 SYNTHESIS OF BENZOQUINONE
Page 313 and 314: SYNTHESIS OF BENZOQUINONES BY OXIDA
Page 339: SYNTHESIS OF BENZOQUINpNES BY OXIDA
Page 351 and 352: Quinone 5,6-Dimethoxy-2hydi oxyquin
Page 353 and 354: Quinone 3-Hydroxythymoqui- J none |
Page 355 and 356: Quinone 2-Methoxy-6-tridecylquinone
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
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THE WOLFF-KISHNER REDUCTION 387 TAB
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THE WOLFF-KISHNER REDUCTION 389 Red
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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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Page 427 and 428:
Page 429 and 430:
DEX Numbers in bold-face type r :ef
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Dialkylaminoquinonedisulfonates, 35
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3-Methylpyrene, preparation by Wolf
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