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SchifFs Base 0-C6H5N=CHC6H4CIf 0-C6H5N=CHC6H4CIf 0-C6H5N=CHC6H4CIf m-C6H5N=CHC6H4Clf W-C6H5N=CHC6H4CIf P-C6H5N=CHC6H4CIf P-C6H5N=CHC6H4CIf 0-C6H5N=CHC6H4OHf 0-C6H5N=CHC6H4OH f W-C6H5N=CHC6H4OHf P-C6H5N=CHC6H4OH f 2',5'-C6H5N=CHC6H3(OH) (CH3) f 2',5'-C6H6N=CHC6H3(OH) (CH3) f p-C6H5N=CHC6H4OCH3f HD6H5N=CHC6H4OCHBf p-C6H5N=CHC6H4OCH3f 3',4'-C6H5N=CHC6H302CH2f P-C6H5N=CHC6H4N (CH8M 0-CH3C6H4N=CHCH2CH(CH3M o-CH3C6H4N=CHC6H5f o-CH3C6H4N=CHC6H5f o-CH3C6H4N=CHC6H5f o-CH3C6H4N=CHC6H5f 2,4'-CH3C6H4N=CHC6H4CHSf 2,4'-CH3C6H4N=CHC6H4CH3f 2,4'-CH3C6H4N=CHC6H4CIf TABLE X—Continued PREPAEATION OF SECONDARY AMINES I. By Reduction of Schiffs Bases Derived frmn Aromatic Amines—Continued Reducing Agent Electrolytic Pb cathode Electrolytic Cu cathode Na-Hg + CH3CH2OH Electrolytic Pb cathode Electrolytic Cu cathode Electrolytic Pb cathode Electrolytic Cu cathode Mg + CH3OH Na-Hg + CH3CH2OH Na-Hg + CH3CH2OH Na-Hg + CH3CH2OH Zn + CH3CO2H Al-Hg Xa-Hg + CH3CH2OH Electrolytic Pb cathode Mg + CH3OH Mg -f CH3OH Mg + CH3OH H2 + Ni Electrolytic Pb cathode Electrolytic Cu cathode H2 -f Ni H2 -f Ni Electrolytic Pb cathode Electrolytic Cu cathode Electrolytic Pb cathode Product 0-C6H5NHCH2C6H4CI 0-C6HsNHCH2C6H4Cl 0-C6H5NHCH2C6H4Cl ^C6H5NHCH2C6H4Cl ^C6H5NHCH2C6H4Cl P-C6H5NHCH2C6H4Cl P-C6H5NHCH2C6H4Cl 0-C6H5NHCH2C6H4OH 0-C6H5NHCH2C6H4OH ^-C6H5NHCH2C6H4OH P-C6H5NHCH2C6H4OH 2',5'-C6H5NHCH2C6H3(OH) (CH3) 2,5,2',5'-C6H5NHCHEC6H3(OH) (CH3)]- CH[C6H3OH(CH3)JNHC6H5 P^C6H5NHCH2C6H4OCH3 P-C6H5NHCH2C6H4OCH3 P-C6H5NHCH2C6H4OCH3 3',4'-C6H5NHCH2C6H3O2CH2 P-C6H5NHCH2C6H4N(CHs)2 o-CH3C6H4NH(CH2)2CH(CH3)2 0-CH3C6H4NHCH2C6H5 0-CH3C6H4NHCH2C6H5 0-CH3C6H4NHCH2C6H5 0-CH3C6H4NHCH2C6H5 2,4'-CH3C6H4NHCH2C6H4CH3 2,4'-CH3C6H4NHCH2C6H4CH3 2,4'-CH3C6H4NHCH2C6H4Cl Yield, % 87 83 38 77 40 63 57 — 88 — — Quantitative 80 — — 99 83 — — 77 48 61 Kef.* 68 68 175 68 68 68 68 65 176 175 176 170 170 177 171 65 65 65 63 68 68 63 173 68 68 68 O t—I 0 > O H HH O Ul
2,4'-CH3C6H4N=CHC6H4CIf 2,4 / -CH3C6H4N=CHC6H4OCH3t ^CH3C6H4N=CH(CHOH)4CH2OH ^-CH3C6H4N=CHC6H5I m-CH3C6H4N=CHC6H6- W-CH3C6H4N=CHC6H5- 3,3'-CH3C6H4N=CHC6H4CH3I 3,3'-CH3C6H4N=CHC6H4CH3- 3,4'-CH3C6H4N=CHC6H4CH3- 3,4'-CH3C6H4N=CHC6H4CH3- 3,4'-CH3C6H4N=CHC6H4CIf 3,4'-CH3C6H4N=CHC6H4CIf p-CH3C6H4N=CHC6H5f p-CH3C6H4N=CHC6H5f p-CH3C6H4N=CHC6H5f p-CH3C6H4N=CHC6H5f p-CH3C6H4N=CHC6H5f 4,3'-CH3C6H4N=CHC6H4CHSf 4,3'-CH3C6H4N=CHC6H4CH3f 4,4'-CH3C6H4N=CHC6H4CH3f 4,4'-CH3C6H4N=CHC6H4CH3f 4,4'-CH3C6H4N=CHC6H4CH(CH3)2f 4,4'-CH3C6H4N=CHC6H4CIf 4,4'-CH3C6H4N=CHC6H4CIf 4,2'-CH3C6H4N=CHC6H4OHf * References 134—180 are listed on p. 255. f These Schiff's bases probably were purified before reduction. Electrolytic Cu cathode Na-Hg + CH3CH2OH H2 + Ni Electrolytic Pb cathode Electrolytic Pb cathode H2+ Ni Electrolytic Pb cathode Electrolytic Cu cathode Electrolytic Pb cathode Electrolytic Cu cathode Electrolytic Pb cathode Electrolytic Cu cathode Electrolytic Pb cathode Electrolytic Cu cathode Mg -f CH3OH H2 + Ni Na-Hg + CH3CH2OH Electrolytic Pb cathode Electrolytic Cu cathode Electrolytic Pb cathode Electrolytic Cu cathode Na-Hg -b CH3CH2OH Electrolytic Pb cathode Electrolytic Cu cathode Na-Hg + CH3CH2OH 2,4'-CH3C6H4NHCH2C6H4Cl 2,4'-CH3C6H4NHCH2C6H4OCH3 ^CH3C6H4NHCH2(CHOH)4CH2OH ^-CH3C6H4NHCH2C6H5 ^CH3C6H4NHCH2C6H5 ^-CH3C6H4NHCH2C6H5 3,3'-CH3C6H4NHCH2C6H4CH3 3,3'-CH3C6H4NHCH2C6H4CH3 3,4'-CH3C6H4NHCH2C6H4CH3 3,4'-CH3C6H4NHCH2C6H4CH3 3,4'-CH3C6H4NHCH2C6H4Cl 3,4'-CH3C6H4NHCH2C6H4Cl P-CH3C6H4NHCH2C6H5 P-CH3C6H4NHCH2C6H5 p,p'-CH3C6H4NHCH(C6H5)- CH(C6H5)NHC6H4CH3 P-CHsC6H4NHCH2C6H5 P-CHsC6H4NHCH2C6H5 P-CH3C6H4NHCH2C6H5 4,3'-CH3C6H4NHCH2C6H4CH3 4,3'-CH3C6H4NHCH2C6H4CH3 4,3,4',3'-CH3C6H4NHCH(C6H4CH3)- CH(C6H4CH3)NHC6H4CH3 4,4'-CH3C6H4NHCH2C6H4CH3 4,4'-CH3C6H4NHCH2C6H4CHg 4,4,4',4'-CH3C6H4NHCH(C6H4CH3)- CH(C6H4CH3)NHC6H4CH3 4,4'-CH3C6H4NHCH2C6H4CH(CHg)2 4,4'-CH3C6H4NHCH2C6H4Cl 4,4,4',4'-CH3C6H4NHCH(C6H4Cl)- CH(C6H4Cl)NHC6H4CH3 4,4'-CH3C6H4NHCH2C6H4Cl 4,4,4',4'-CH3C6H4NHCH(C6H4Cl)- CH(C6H4Cl)NHC6H4CH3 4,2'-CH3C6H4NHCH2C6H4OH 30 — 52 77 51 — 83 61 63 51 57 32 97 75 10 — — 73 53 20 91 57 24 — 59 10 16 20 Good 68 177 66 68 68 173 68 68 68 68 68 68 68 68 65 173 178 68 68 68 68 174 68 68 176 W H > W 15 O O )-< Ul W W « a o < > > H O 3
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.,
Page 13 and 14:
DIENE SYNTHESIS I 7 and IV for thes
Page 15 and 16:
DIENE SYNTHESIS I 9 tion of the com
Page 17 and 18:
Maleic anhydride Fumaric anhydride
Page 19 and 20:
DIENE SYNTHESIS I 13 jugated system
Page 21 and 22:
DIENE SYNTHESIS I 15 Mesaconic (met
Page 23 and 24:
DIENE SYNTHESIS I 17 An interesting
Page 25 and 26:
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
Page 33 and 34:
DIENE SYNTHESIS I 27 Certain types
Page 35 and 36:
DIENE SYNTHESIS I 29 Hydrocarbons c
Page 37 and 38:
DIENE SYNTHESIS I 31 Diels-Alder re
Page 39 and 40:
DIENE SYNTHESIS I 33 give LXXX. If
Page 41 and 42:
DIENE SYNTHESIS I 35 Numerous other
Page 43 and 44:
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
Page 49 and 50:
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
Page 55 and 56:
Cycloheptatriene DIENE SYNTHESIS I
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BIENE SYNTHESIS I 51 TABLE V—Cont
Page 59 and 60:
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
Page 65 and 66:
DIENE SYNTHESIS I 59 422 Diels and
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DIENE SYNTHESIS II 61 PAGE TABLKs O
Page 69 and 70:
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
Page 77 and 78:
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
Page 89 and 90:
DIENE SYNTHESIS II 83 covered as th
Page 91 and 92:
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
Page 97 and 98:
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
Page 103 and 104:
1-Diethylaminobutadiene 1,1-Dimeth
Page 105 and 106:
1-Methylbutadiene (piperylene) l-Me
Page 107 and 108:
1,5,5,6-Tetramethylcyclohexadiene (
Page 109 and 110:
1-Methyl-l-phenylbtrfcadiene l-Met
Page 111 and 112:
Benzalacetophenone Bicyclohexenyl r
Page 113 and 114:
f$-Benzoylacrylic acid, 2, b-dimeth
Page 115 and 116:
Bicyelohexenyl c r 2,3-Dimethylbuta
Page 117 and 118:
Isoprene Cinnamic acid,2,6~ dimetho
Page 119 and 120:
Isoprene Cinnamic acid,omeihoxy- (t
Page 121 and 122:
Coumann Butadiene 2,3-Dimethylbutad
Page 123 and 124:
1,3-Dimethylbutadiene 1,4-Dimethyl
Page 125 and 126:
1,1,3-Trimethylbutadiene 1,1,4-Tri
Page 127 and 128:
2,3-Dimethylbutadiene Croio7toladon
Page 129 and 130:
2,3-Dimethylbutadiene2,3-Diphenylbu
Page 131 and 132:
Cyclopentadiene 2,3-Dimethylbutadie
Page 133 and 134:
Z}4rDihydro-5-bromo- 1\8-dimethoxy-
Page 135 and 136:
Z^Dihydro-l-ftieihoxy-2-naphthoic a
Page 137 and 138:
Ethyl ethytidenemalonate Butadiene
Page 139 and 140:
1,4-Diphenylbutadiene2,3-Diphenylbu
Page 141 and 142:
6 The product gradually decomposes
Page 143 and 144:
Cyclohexadiene Cyclopentadiene 2,3-
Page 145 and 146:
p-Nitrostyrenej 3,4-cfomethoxy- 2,3
Page 147 and 148:
Dihydrothiophene-1 - dioxide Butadi
Page 149 and 150:
Piperylcyclone Tetraphenyleyelopent
Page 151 and 152:
AUyI iodide Cyclopentadiene AUyI is
Page 153 and 154:
Tetraphenylcyclopentadienone Pheney
Page 155 and 156:
Indene a,a , -Diphenyl-/3,j3'isoben
Page 157 and 158:
1,5,5-Trimethyleyclopentadiene Tri
Page 159 and 160:
Addends Acetylene Tetraphenylcyelop
Page 161 and 162:
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
Page 169 and 170:
I-* SO N-ce-Dimethylindole 3,5-Dim
Page 171 and 172:
Oi N-Methylindole a-Methylpyrrole N
Page 173 and 174:
OS Quinaldine Quinoline CX | JCH. j
Page 175 and 176:
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 183 and 184:
Page 185 and 186:
Page 187 and 188:
Page 189 and 190:
Page 191 and 192:
Page 193 and 194:
Page 195 and 196: 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 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: C6H5N-=CHCH2CH(CH3)2f C6H5N=CH(CHOH
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
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 315 and 316:
Page 317 and 318:
Page 319 and 320:
Page 321 and 322:
Page 323 and 324:
Page 325 and 326:
Page 327 and 328:
Page 329 and 330:
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
Page 341 and 342:
Page 343 and 344:
Page 345 and 346:
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
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
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
Page 411 and 412:
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
Page 423 and 424:
THE WOLFF-KISHNER REDUCTION 417 133
Page 425 and 426:
Page 427 and 428:
Page 429 and 430:
DEX Numbers in bold-face type r :ef
Page 431 and 432:
Dialkylaminoquinonedisulfonates, 35
Page 433 and 434:
3-Methylpyrene, preparation by Wolf
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