Organic Reactions Volume 4 - Sciencemadness Dot Org

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346 ORGANIC REACTIONS Quinone 2,5-Di-p-phenetylquinone 2,5-Diphenoxyquinone 2- (a,a-Diphenylethyl) - 5-methoxyquinone 2- (o;,/3-Diphenylisopr opyl) -5-methoxyquinone 2,5-Di-p-toloxyquinone Ethoxyquinone i 2-Ethoxy-6-methoxy~ I quinone 1 5-Ethoxy-6-methoxytoluquinone 2-E tho xy-6-pr opylquinone 5-Ethoxytoluquinone 3-E thoxy- m-xyloquinone 2-Hy dr oxy ~5-methoxyquinone2-Hydroxy-6-methoxyquinone 3-Hydroxy-5-meth- J oxytoluquinone 1 3-Hydroxy-6-methoxytoluquinone 5-Hydi oxy~3~methoxytoluquinone6-Hydroxy-5-methoxytolu quinone 3-Hy dr oxy-5-methoxym-xyloquinone Hydroxymethylquinone Hydroxyquinone TABLE III*—Continued HYDROXYQITINONES AND DERIVATIVES Substance Oxidized Condensation product of quinone and phenetole2,5-Diphenoxyhydroquinone 2- (a, a-D iphenylethyl) - 1,4,5-trimethoxyben- 2- (a,/3-Diphenylisopropyl)-1,4,5-trimethoxybenacne 2,5-D i-p-toloxyhydroquinone 2,4-Diethoxyaniline 2-Ethoxy-4-hydroxyaniline Phenyl-(2,4-dimethoxy~ 6-othoxyphenyl)-carbin ol 3-M ethoxy-5-ethoxyphenol5-Mcthoxy-6-othoxy-mtoluidine1,2,4-Tiiethoxy-epropylbenzene 2,4'~Dimethyl-4-amino~ 5-ethoxydiphonylamine 2,4',6-Trimethyl-4~ amino-5-ethoxy-diphenylamine2-Hydroxy-5-methoxyhydroquinone2,4-Dihydroxy-6-methoxyaniline 3-Hydroxy-5~mothoxy~ toluhydroquinone 3-Hydroxy~4-amino-5methoxy-o-cresol 2-Hydroxy-3-amino- 4,6-dimethoxy toluene 3-Hydroxy~6-methoxytoluhydroquinone5~Hydroxy-3~methoxytoluhydroquinone4~Amino-5-hydroxy-6meth oxy-m-cr esol 3~Hydroxy~4-amino-5methoxy-nc .-m-xylol Gentisylalcohol I Hydroxyhydroquinone Oxidizing Agent FeCl3 CrO3 (AcOH) HNO3 (AcOH) HNO3 (AcOH) CrO3 (dil. AcOH) K2Cr2O7 (H2SO4) Na2Cr2O7 (H2SO4) CrO3 (AcOH) CrO3 (AcOH) Na2Cr2O7 (H2SO4) HNO3 (25%) K2Cr2O7 (H2SO4) K2CB2O7 (H2SO4) Air (pH 8) ' FeCl3 FeCl3 FeCl3 FeCl3 Air (pH 8) FeCl3 FeCl3 FeCl3 Pb(OAc)4 Ag2O * See p. 315 for explanation of system and abbreviations in tables, t References 280-323 are listed on p. 350. — — — — Yield Neaily quant. — — 20% (or.) 29% (cr.) _ 48% *~ 95% 40% Nearly quant. — — 92% (o.) 47% — 80% 70% 60% References f 113 297 266 266 133 298 299 261 261 251 . 311 300 301 252 271 249 (y.),250, 296 302 274 252 249 312 303 303a 39, 59 (y.)
Quinone 3-Hydroxythymoqui- J none | 3~Hydroxy-6~chloro~ thyrnoquinone 6- Hydroxythymoqui- 3- Hydroxy-6-chlorotoluquinone 5-Hydroxytoluquinonc 5-Hydroxy-3,6-dichlorotoluquinone6-Hydroxy-3-ohlorotoluquinone 6-Hydroxy~5-chloro~ toluquinone 6-Hy droxy-3,5-dichlorotoluquinoneHydroxytriphenylquinone f 3-Hydroxy-m-xyloqui- J none I 2-Methoxy-6-amyl quinone 2-Methoxy-6-amyl-5~ J bromoquinone j 2-Methoxy-6-(3,4,5-trichloro-2,6-dimethoxyphenoxy)-3,5-dichloroquinone2-Methoxy-6-(3,4,5-tribromo-2,6-dimethoxyphenoxy)-3,5-dibromoquinone2-Methoxy-6~dodeeylquinone2-Methoxy-6-hendecylquinone SYNTHESIS OF BENZOQUINONES BY OXIDATION 347 r I TABLE Ill—Continued HYDROXYQUINONES AND DERIVATIVES Substance Oxidized 3-Hydroxycarvacrol 3-Hydroxy-6-aminocarvacrol 4,6-Diaminothymol 2,6-Diamino-3-ethoxyp-cymene Menthone, 2,3-dihydromenthone or menthol 2,6~Diamino-3-chloro-p~ cymene 2,6~Diamino-3~chloro- ' p-cymene 4,6-Diaminocar vacr ol 3-Hydroxy-6-chlorotoluhydroquinone5-Hydroxytoluhydroquinone 5-Hydr oxy-3,6-diohlorotoluhydroquinone I 4,6~Dihydroxy-3-cmoroo-toluidine4,6-Dihydroxy~o~toluidine hydrochloride I 2,4,6-Trichloro-5-methylresorcinol Ethyl triphenylgentisate 2,4-Diaminomesitylene 3,5-Dimethyl~ A 2 -cy clohexenone1-Amyl-3,5-dimethoxybenzenel-Amyl-2-bromo-3,5dimethoxybenzeiiel',4',3~Tribromo-3'methyl-2-amyl-l,4,5'~ trimethoxydiphenyl ether 2,6-Dimethoxy-3,4,5trichlorophenol 2,6-Dimethoxy-3,4,5tribromophenol l,3-Dimethoxy-5-dodecylbenzenel,3-Dimethoxy-5-hendecylbenzene * References 280-323 are listed on p. 350. Oxidizing Agent HNO3 or H2O2 HNO3 FeCl3 FeCl3 SeO2 Na2Cr2O7 (H2SO4) Na2Cr2O7 (H2SO4) FeCl3 HNO3 (sp. gr. 1.4) FeCl3 HNO8 (sp. gr. 1.4) K2Cr2O7 (H2SO4) K2Cr2O7 (H2SO4) • Alkaline potassium ferrocyanide Air in alkaline medium K2Cr2O7 (H2SO4) or FeCl3 SeO2 (AcOH) Na2Cr2O7 (AcOH) Na2Cr2O7 (AcOH) Na2Cr2O7 (AcOH) CrO3 (50% AcOH) CrO3 (50% AcOH) PbO2 (AcOH) NaNO2 (AcOH) PbO2 (benzene) CrO3 CrO3 — _ — Yield 2-8% Poor Very poor — —, 90% — 6% — 12% 5% — __ Poor 30% (o.) 23% 50% 40% 60% 25% 70% 45% _ References* 285 285 4 30 304 30 30 31 66 248, 309a (y.) 32 277 277 305 238a 29 306 262, 263 262 310 16 16 16 16 16 264 264
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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 187 and 188:
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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
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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
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 and 340: SYNTHESIS OF BENZOQUINpNES BY OXIDA
Page 351: Quinone 5,6-Dimethoxy-2hydi oxyquin
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
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
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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:
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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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