Organic Reactions Volume 4 - Sciencemadness Dot Org

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Nitro Compound or Amine Used CH3CHOHCH2NH2 CH3CHOHCH2NH2 CH3CHOHCH2NH2 CH3CHOHCH2NH2 CH3CHOHCH2NH2 CH3CHOHCH2NH2 CH3CHOHCH2NH2 CH3CHOHCH2NH2 HOCH2CH(CH3)NH2 HOCH2CH(CH3)NH2 HOCH2CH(CH3)NH2 HOCH2CH(CH3)NH2 HO(CH2)3NH2 HO(CH2)3NH2 HO(CH2)3NH2 HO(CH2)3NH2 HOCH2CH(CH2CH3)NH2 HOCH2CH(CH2CH3)NH2 HOCH2CH(CH2CH3)NH2 (CH3)2COHCH2NH2 (CHa)2COHCH2NH2 (CHs)2COHCH2NH2 TABLE X—Continued PEEPABATION OF SECONDARY AMINES E. From Primary Aliphatic Amines or Nitro Compounds and Ketones—Continued Carbonyl Compound CH3CO(CH2)5CH3 CH3(CH2)3CO(CH2)3CH3 CH3(CH2)4CO(CH2)4CH3 CH3(CH2)5CO(CH2)5CH3 CH3(CH2)6CO(CH2)6CH3 CH3(CH2)8CO(CH2)8CH3 Cyclohexanone CH2CH2 H3CCH CO CH2CH2 CH3CH2COCH2CH3 CH3(CH2)2CO(CH2)2CH3 CH3(CH2)3CO(CH2)3CH3 Cyclohexanone CH3CO(CH2)4CH3 CH3(CH2)2CO(CH2)2CH3 CH3CO(CH2)5CH3 Cyclohexanone CH3COCH3 CH3(CH2)3CO(CH2)3CH3 Cyclohexanone CH3COCH3 CH3CH2COCH2CH3 CH3CO(CH2)4CH3 Reducing Agent H2 + Pt H2 +Pt H2 +Pt H2+Pt H2+Pt H2+Pt H2+Pt H2 +Pt H2+Pt H2+Pt H2 +Pt H2+Pt H2+Pt H2+Pt H2+Pt H2+ Pt H2+ Pt H2+Pt H2+Pt H2+Pt H2+ Pt H2+Pt Products Isolated CH3CHOHCH2NHCH(CH3) (CH2)5CH3 CH3CHOHCH2NHCH[(CH2)3CH3]2 CH3CHOHCH2NHCH[(CH2)4CH3]2 CH3CHOHCH2NHCH[(CH2)5CH3j2 CH3CHOHCH2NHCHt (CH2)6CH3]2 CH3CHOHCH2NHCH[(CH2)8CH3]2 CH3CHOHCH2NHC6H11 CH2CH2 CH3CHOHCH2HNCH CHCH3 CH2CH2 HOCH2CH(CH3)NHCH(CH2CH3)2 HOCH2CH(CH3)NHCH[(CH2)2CH3]2 HOCH2CH(CH3)NHCH[(CH2)3CH3J2 HOCH2CH(CH3)NHC6H1I HO(CHS)3NHCH(CH3) (CHg)4CH3 HO(CH2)3NHCH[(CH2)2CH3]2 HO(CH2)3NHCH(CH3) (CH2)SCH3 HO(CH2)SNHC6HH HOCH2CH(CH2CH3)NHCH(CHS)2 HOCH2CH(CH2CH3)NHCH[(CH2)3CH3]2 HOCH2CH(CH2CH3)NHC6H11 (CH3)2COHCH2NHCH(CH3)2 (CH3)2COHCH2NHCH(CH2CH3)2 (CH3)2COHCH2NHCH(CH3) (CH2)4CH3 Yield, % 96 81 88 80.5 94 68 95 93 64 84 72 82 90 98 90 78 93 50 68 96 96 98 Ref.* 59 59 59 59 59 59 59 59 60 60 60 60 61 61 61 61 60 60 60 60 60 60 to to O I—! O & > 9 f—i O %
(GHg)2COHCH2NH2 (CHs)2COHCH2NH2 CH3CHOHNH2 H2N(CHs)2NH2 CH3CO(CH2)5NH2 CgHgCH2NH2 C6H5CO(CH2)SNH2 H2NC= 0-&- =CCH3 NCH3 N C6H5 ONC=CCH3 I O=C NCH3 N C6H5 H2NC=CCH3 o=A NCH3 N C6H5 ONC=CCH3 I i O=C NCH3 C6H5 CH3CO(CH2)5CH3 Cyclohexanone CH3COCO2H C6H5COCH3 C6H5CH2COCH3 CH3COCH3 CH3COCH3 * References 134-180 are listed on p. 255» CH3COCH2CH3 CH3COCH2CH3 I H2 + Pt -H2 + Pt H2 + Pt H2 + Ni Na + CH3- CH2OH I H2 + Pt Na + CH3- CH2OH I H2 + Pt or H2 + Ni H2 + Pt H2 + Pt H2+ Pt (CH3)2COHCH2NHCH(CH3)(CH2)5CH3 (CH3)SCOHCH2NHC6H11 CH3CH2NHCH(CH3)CO2H H2N(CH2)SNHCH(CH3)C6H5 C6H5CH(CH3)NH2 H3CCHCH2CH2X I >CH2 NHCH2CH2^ C6H5CH2CH(CH3)NHCH2C6H5 H5C6CHCH2CH2x i >CH2 V NHCH2CH2' (CH3)2CHHNC= =CCH3 O=C NCH3 (CH3)2CHHNC=i=CCH3 C=A NCH3 N C6H5 CH3CH2CH(CH3)HNC=: o4 CH3CH2CH(CH3)HNC= =CCH3 NCH3 x / N C6H5 ==CCH3 O=C NCH3 N C6H5 87 37 55 Almost quantitative Almost quantitative Almost quantitative Almost quantitative 60 60 62 137 150 149 150 31 31 31 31 g (—< O O H-! ft XJl W Kj cl O H O fcO ISD O3
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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
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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
Page 177 and 178: 1,3-Dimethylbutadiene 1,1,3-Trimet
Page 179 and 180: DIENE SYNTHESIS II 110 Diels and Al
Page 181 and 182: 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: HO(CH2)2NH2 HO(CHa)2NH2 HO(CH2)2NH2
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 and 238: HN=C(CH3)CO2H CH2 SehifPs Base / \
Page 239 and 240: CH3CH2N=CHC6H5J CH3(CH2)2N=CHCH3f C
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
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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
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Page 367 and 368:
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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
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ROSENMUND REDUCTION 371 TABLE I ALI
Page 379 and 380:
Acid Chloride Benzoyl chloride p-Ca
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Acid Chloride 3-Furoic- 4~Carbometh
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ROSENMUND REDUCTION 377 106 Shoesmi
Page 385 and 386:
THE WOLFF-KISHNER REDUCTION 379 INT
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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
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THE WOLFF-KISHNER REDUCTION 391 Dir
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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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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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