Organic Reactions Volume 4 - Sciencemadness Dot Org

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44 ORGANIC REACTIONS Butadiene Butadiene Butadiene Butadiene TABLE III ADDTJCTS FROM MALBIC ANHYDRIDE WITH ACYCLIC COMPOUNDS Diene tfrans-l,3-Pentadiene(frans-piperylene) tfrans-Piperylene Piperylene 2-M cthy 1-1 ,3-butadiene (isoprene) Isoprene Isoprene 1,3-Hexadiene 2,4-Hexadiene 2,4-Hexadicne 2,4-Hexadiene 2,4-Hexadiene 2-Methyl-l,3-pentadiene 2-Methyl-l,3-pentadiene 2~Methyl-l,3-pontadiene 2-Methyl-l,3-pentadieno 3-Methyl-l,3~pentadiene 4-Methyl-l,3-pentadicne 2,3-Dimethyl-l,3-butadiene 2,3-Dimethyl-l,3-butadiene 2,3-Dimethyl-l,3-butadiene 2,3-Dimethyl-l ,3-butadiene 2,3~Dimethyl-l,3-butadiene 2,4-Heptadiene 5-M ethyl-1,3-hexadiene 3-Methyl-2,4-hexadicne 2,4-Dimethyl-l ,3»pentadicne 2,4-Dimothyl-l,3-pentadiene 4-Ethyl-l,3-hexadiene 2-Cyclopropyl-l,3-butadicne 2,6-Dimethyl-3,5-octadiene 7-Mcthyl-3-methylene-l,6-octadienc (myrcene) Myrcene Myrcene 5-Methyl-4~isopropyl-l,3-hexadieno 1-Phenyl~l,3~butadiene l-Phenyl-l,3-butadiene 1-Phenyl-l ,3-pentadiene 4-Phenyl-l,3-pentadiene l-(3 ',4'-MethylenedioxyphenyD- 1,3-butadiene | 2-Methyl-l-phenyl-l,3-butadiene 6-Pheny 1-1,3-hexadiene 4-p-Tolyl-l,3-pentadiene l-(3',4'-Dimethoxyphenyl)-l,3-butadiene t MoIeB Anhydride per Mole Diene 0.88-1.1 1 0.86 — 1 1.2 _. — 1 1 — 1 — 1 1 1 1 1 1 — 1 — 1 I 1 — __ _ — 1 1 1 — 1 1 1 0.66 2 1 1 0.5 1.5 Solvent Benzene Benzene Benzene Benzene Benzene None Benzene Benzene Benzene Benzene — Benzene Benzene — Benzene Benzene Dioxano Benzeno Benzene Benzene — Benzene Benzene Dry benzone Benzeno Water (omulsion) — Benzene __ — Benzene — Benzene — None None None _ None — None Benzene Xylene Dry benzene Xylene Benzene Xylene Reaction Temperature and Time Room temp. (12 hr.); 100° (5 hr.) Room temp. (24 hr.) Room temp. (12 hr.); 100° (5 hr.) Room temp. (2 days); 100° (8hr.) 0° (5 days) 100° (2.5 hr.) Room temp. Room temp. Gentle heat 0° (12 hr.); 100° (several hours) — Room temp. (24 hr.) — — 0° (12 hr.); 100° (several hours) Room temp. 4° Room temp. (1 week) 0° (12 hr.); 100° (several hours) 0° (12 hr.); 100° (several hours) — 0° (12 hr.); 100 (several hours) Room temp. Room temp. (24 hr.) Heated 40° (12 hr.) — Room temp. (> 1 week) __ — Room temp. (2-3 days) __ — Warm Warm gently Fuse __ Warm Heat Warm 100-105° (2 hr.) Reflux (3 hr.) 100° (6 hr.) Room temp. (4 days) 105-110° (2 hr.) Reflux (7.5 hr.) Yield % Quant. Quant. 90 — 95 97 — — Quant. — —, Quant. — 77 — Quant. 96 — Quant. — Quant. — Good — Quant. Quant. — 6 Quant. — 20 14 55 Ref.* 5 148 323 324 131 140 6 6 324 131 135 6 135 325 131 6 132 134 131 131 137 131 6 148 324 320 135 134 135 326 6 137 327 19 6,328 * References 324-434 are listed on pp. 57-59. f Piperonylallylcarbinol which was dehydrated under the reaction conditions was employed. 1 3,4-Dimethoxyphenylallylcarbinol which was dehydratod under the reaction conditions was employod. 329 330 137 151 331 151 18 333 331 136 18 333
DIENE SYNTHESIS I 45 TABLE III—Continued ADDUCTS FROM MALEIC ANHYDRIDE WITH ACYCLIC COMPOUNDS Diene 4-(2',4'-Dimetnylphenyl)-l,3-pentadiene l-Butadienyl-2~vinyl-3-cyclohexene l-a-Naphthyl-l,3-butadiene t l-cs-Naphthyl-l.S.-butadiene 3-ter
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
Page 45 and 46: DIENE SYNTHESIS I 39 Indole derivat
Page 47 and 48: DIENE SYNTHESIS I 41 anhydride. In
Page 49: DIENE SYNTHESIS I 43 tetrahydronaph
Page 53 and 54: DIENE SYNTHESIS I 47 TABLE IV ADDtr
Page 55 and 56: Cycloheptatriene DIENE SYNTHESIS I
Page 57 and 58: BIENE SYNTHESIS I 51 TABLE V—Cont
Page 59 and 60: DIENE SYNTHESIS I 53 TABLE VI ADDTJ
Page 61 and 62: BIENE SYNTHESIS I 55 TABLE VII—Co
Page 63 and 64: DIENE SYNTHESIS I 57 REFERENCES TO
Page 65 and 66: DIENE SYNTHESIS I 59 422 Diels and
Page 67 and 68: DIENE SYNTHESIS II 61 PAGE TABLKs O
Page 69 and 70: DIENE SYNTHESIS II 63 The configura
Page 71 and 72: DIENE SYNTHESIS II 65 Aromatic comp
Page 73 and 74: DIENE SYNTHESIS II 67 55%). 13 Cycl
Page 75 and 76: H8Cr H8C JCO2H XSV iOCH, DIENE SYNT
Page 77 and 78: DIENE SYNTHESIS II 71 additions wit
Page 79 and 80: DIENE SYNTHESIS II , 73 been report
Page 81 and 82: DIENE SYNTHESIS II 75 drogenation u
Page 83 and 84: DIENE SYNTHESIS II 77 Allyl, Vinyl,
Page 85 and 86: DIENE SYNTHESIS II 79 (XLVII) that
Page 87 and 88: ~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
Page 93 and 94: DIENE SYNTHESIS II 87 or even preve
Page 95 and 96: DIENE SYNTHESIS II 89 SELECTION OF
Page 97 and 98: DIENE SYNTHESIS II 91 liquid separa
Page 99 and 100: Acetylenic Dienophile Ethyl acetyle
Page 101 and 102:
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:
Page 197 and 198:
Page 199 and 200:
Page 201 and 202:
Page 203 and 204:
Page 205 and 206:
Page 207 and 208:
Page 209 and 210:
Page 211 and 212:
Page 213 and 214:
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 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 261 and 262:
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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