Organic Reactions Volume 4 - Sciencemadness Dot Org

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Amine, Nitro, Nitroso, or Azo Compound Used P-H2O3AsC6H4NH2 Qj-Ci0H7NH2 Q-C10H7NH2 Qj-C10H7NO2 Qr-C10H7NO2 Q1-C10H7NH2 /S-C10H7NH2 /S-C10H7NH2 0-C10H7NH2 /S-C10H7NH2 CHsOf^^V^ NO2 N Amine, Nitro or Nitroso Compound Used 04H5NO2 C6H5NH2 G6HsNO2 TABLE X—Continued PREPARATION OF SECONDARY AMINES F. From Primary Aromatic Amines, Nitro, Nitroso, or Azo Compounds and Aldehydes—Continued Carbonyl Compound CH3CHO CH3CHO CH3(CHg)2CHO CH3(CH2)2CHO CH3(CHg)3CHO C6H5CHO CH2O CH3CHO CH3(CH2)2CHO C6H5CHO CH3CO(CH2V N(CH2CH3)2 Reducing Agent H2 + Ni H2 + Ni H2 + Ni H2 + Ni H2 + Ni H2+Ni Zn + NaOH H2 + Ni H2 + Ni H2 + Ni H2+Pd Products Isolated P-H2O3AsC6H4NHCH2CH3 CL- C10H7NHCH2CHg Qr-C10H7NH (CH2) 3CH3 «-C10H7NH(CH2)3CH3 OJ-CIOH7NH (CH2) 4CH3 C-C10H7NHCH2C6H5 /S-C10H7NHCH3 /S-C10H7NHCH2CH3 /5-C10H7NH(CH2)3CH3 /S-C10H7NHCH2C6H5 CH 80f^V^ NHCH(CH3) (CH2)3N(CH2CH3)2 G. From Primary Aromatic Amines, Nitro, or Nitroso Compounds and Ketones Carbonyl Compound CH3COCH3 CH3COCH3 CH3COCH3 Reducing Agent H2+ Pt Zn + HCl H2 +Pt C6H5NHCH(CHs)2 C6H5NHCH(CH3)2 None Products Isolated Yield, % 5 88 80 60 43 24 — 64 63 58 87 Yield, % 53 31 O Ref.* 41 36 33,36 43 43 33,36 39 36 36 36 154 Ref.* 2 42 52 OO
CeHgNHs C6H5NH2 C6HgNH2 C6H5NH2 P-CH3C6H4NH2 2,4,6-(CH3)SC6H2NH2 0-ClC6H4NH2 0-HOC6H4NO2 m-HOC6H4N02 P-HOC6H4NO P-HOC6H4NO P-HOC6H4NH2 P-HOC6H4NO2 P-HOC6H4NH2 P-HOC6H4NO2 P-HOC6H4NO2 P-HOC6H4NO2 P-HOC6H4NO2 P-CH3OC6H4NO2 l-HO-2,4-C6Hs(N02)2 P-CHSCHSOC6H4NH2 l-CH3CH20-2,4-CeHs- (NOs)2 0-H2NC6H4NO2 WZ-H2NC6H4NO2 P-H2NC6H4NO2 P-C6H4(NHs)2 P-C6H4(NHs)2 P-H2NC6H4NO2 P-C6H4(NH2)S Cyclohexanone CHsCO(CHs)S- N(CH2CHg)2 C6HgCOCOCH3 C6H5COCOCH3 P-CH3OC6H4COCOCH3 CH3COCH3 CH3CO(CH2)S- N(CH2CHs)2 CH3COCH3 CH3COCH3 CH3COCH3 CH3COCH3 CH3COCH3 CH3COCH3 CHsCOCH3 CHsCOCH2CH3 CHsCH2COCH2CHs Menthone CeH5COCH3 CH3CO(CHs)2- N(CH2CH3)2 CH3COCH3 CH3(CH2)2COCOCH3 CH3COCH3 CH3COCH3 CH3COCH3 CH3COCH3 CH3COCH3 CH3COCH3 CH3COCHSCHS CH3COCH2CH3 * References 134-180 axe listed on p. 255. H2+Pt H2 + Ni H2+Pd H2+Pd H2+Pd Zn + HCl Zn + HCl H2+ Pt H2+Pt H2+Pt H2+ Pt H2+Pt H2 +Pt H2+ Pt H2+Pt H2 +Pt H2+Pt H2+Pt H2+Ni H2+Pt H2+ Pd H2+ Pt H2+ Pt H2+Pt H2 +Pt H2+Pt H2 + CuO, Cr2O3 + BaC H2 + Pt H2 + CuO, Cr2O3 + BaC C6HgNHC6Hn C6HgNHCH(CH3) (CH2)SN(CH2CHs)2 CeHgCOCH(CHs)NHC6H5 C6HgCHOHCH(CH3)NHC6Hg P^-CH3OC6H4COCH(CH3)NHC6H4CH3 2,4,6-(CH3)3C6H2NHCH(CH3)2 0-ClC6H4NHCH(CHs) (CH2)3N (CH2CHs)2 None None P-HOC6H4NHCH(CHs)2 P-HOC6H4NHCH(CHS)2 p-HOC6H4NHCH(CH3)2 P-HOC6H4NHCH(CHs)2 None P-HOC6H4NHCH(CHS)CH2CH3 P-HOC6H4NHCH(CH2CHS)2 None None p-CH3OCeH4NHCH(CH3)(CH2)2N(CH2CH3)2 l-HO-2,4-H2NC6H3NHCH(CH3)2 P-CH3(CH2)SCOCH(CH3)NHC6H4OCH2CH3 None 0-C6H4(NH2J2 0-H2NC6H4NHCH(CHg)2 m-C6H4(NH2)2 p-CeH4[NHCH(CH3)2]2 P-C6H4[NHCH(CH3)S]2 p-CeH4[NHCH(CH3)2]2 P-C6H4[NHCH(CH3)CH2CH3]S P-C6H4[NHCH(CHS)CH2CHS]2 — 86 49 46 49 18 67 O O 60,0 54 50 45 — 34 60 O O 80-100 41 O 35 10 50 80 40 — 70 50 11 51 28 28 28 42 51 52 52 49, 53, 54 52 49 52, 53, 54 50 52, 53, 54 52 52 52 154 52 28 52 44 44 44 44 155 44 155 CO
Page 1 and 2:
Organic Reactions VOLUME IV EDITORI
Page 3 and 4:
PREFACE TO THE SERIES In the course
Page 5 and 6:
CONTENTS CHAPTER PAGE 1. THE DIELS-
Page 7 and 8:
CHAPTER 1 THE DIELS-ALDER REACTION
Page 9 and 10:
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
Page 19 and 20:
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
Page 27 and 28:
CH C2H5 I CH2 XXX DIENE SYNTHESIS I
Page 29 and 30:
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
Page 107 and 108:
1,5,5,6-Tetramethylcyclohexadiene (
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1-Methyl-l-phenylbtrfcadiene l-Met
Page 111 and 112:
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
Page 131 and 132:
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
Page 137 and 138:
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
Page 155 and 156:
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)
Page 163 and 164:
Cyclopentadiene 9,10-Dibromoaiithra
Page 165 and 166:
Propargyl aldehyde 2,3-Dimethylbuta
Page 167 and 168:
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
Page 173 and 174:
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
Page 179 and 180:
DIENE SYNTHESIS II 110 Diels and Al
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PREPARATION OF AMINES BY REDUCTIVE
Page 183 and 184: 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: P-HOC6H4NH2 P-HOC6H4NH2 - P-HOC6H4N
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
Page 281 and 282: THE SYNTHESIS OF BENZOINS 275 Symme
Page 283 and 284: 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
Page 307 and 308:
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 319 and 320:
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Page 323 and 324:
Page 325 and 326:
Page 327 and 328:
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Page 331 and 332:
Page 333 and 334:
Page 335 and 336:
Page 337 and 338:
Page 339 and 340:
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
Page 353 and 354:
Quinone 3-Hydroxythymoqui- J none |
Page 355 and 356:
Quinone 2-Methoxy-6-tridecylquinone
Page 357 and 358:
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
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
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 and 408:
Formula Ci3H22O C13H10O3 Ci3Hi8O3 C
Page 409 and 410:
Formula CI6HHO2 CI6HHO3 CI6H24O3 C1
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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
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THE WOLFF-KISHNER REDUCTION 417 133
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Page 429 and 430:
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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