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CH3CHO CH3(CHa)2CHO (CHs)2CHCH2CHO Carbonyl Compound CH3(CH2)5CHO (CH3)2O=CH(CH2)2C(CH3)==CHCH0 (CH3)2C=CH(CH2)2C(CH3)=CHCHO C6H5CHO C6H5CHO C6H5CHO 0-CH3C6H4CHO 0-ClCeH4CHO Furfural furfural TABLE X PREPARATION OF SECONDARY AMINES A. From Ammonia and Aliphatic Aldehydes Reducing Agent H2 -f Ni H2 + Ni H2 + Ni H2+ Pt H2+Pt H2 + Pt Products Isolated CH3CH2NH2 (CH3CHz)2NH (CH3CH2)gN CH3(CHs)3NH2 [CH3(CH2)Sl2NH [CH3(CH2)3]3N [(CH3)2CH(CH2)2]2NH (CH3)2CH(CH2)2NH2 [CH3(CH2)6]2NH [(CH3)2CH(CH2)3CH(CH3)(CH2)2]2NH [(CH3)2CH(CH2)3CH(CH3)(CH2)2]2NH B. From Ammonia and Aromatic Aldehydes H2 + Ni H2 H2 H2 + Pt + Pd + Ni H2 + Ni H2 + Ni H2+ Ni (C6H5CHs)2NH C6H5CH2NH2 (C6H6CH2J2NH (C6H5CH2)2NH (o-CHgCeH^CHjOaNH D-CH3C6H4CH2NH2 (0-ClC6H4CHs)2NH 0-GlGsH4PH2NH2 Difurfurylamine Furfurylamine Difurfurylamine Yield, % 20,4,f-f 50, 68,f 84f 20,2,tl6t 15-31, —+ 17-40, 80 t 8-22, 2Of 27 15 — 23 81,81 12,17 82,59 11, 14 85 4 66, 66 12, 12 Ref.* 16, 17, 19 16, 19 18 20 18 20 10,21 11 134 10,21 10 10,21 21 to O HH O > Cl H l-H O
CH3COCH3 CH3COCH3 CH3COCH2CH3 CH3COCH2CH3 CH3CHaCOCH2CH3 Cyclohexanone Cyclohexanone CH3COCH2CH2COCH3 C6H5COCH3 Nitro Compound or Amine Used CH3NH2 CH3CH2NH2 CH3CH2NH2 C. From Ammonia and Ketones H2+Pt H2+Pt H2+Pt H2 H2 H2 H2 H2 + Pt + Pt + Pt + Pt + Ni H2+Pt [(CHs)2CH]2NH [(CHs)2CH]2NH [CHsCH2CH(CHs)]2NH [CH3CH2CH(CHs)J2NH [(CH3CH2)2CH]2NH Dieyclohexylamine Dieyclohexylamine CH CH H3O i NH CH2- CCH3 -CH2 H3CCH ;CCI CHCH3 NH [C6H5CH(CH3)I2NH D. From Primary Amines or Nitro Compounds and Aldehydes Carbonyl Compound O OO W WW O OO W W O O Reducing Agent Zn + HCl H2 + Ni H2+ Pt * References 134-180 are listed on p. 255. t In the presence of ammonia plus the primary amine isolated from a previous run. (CH3)2NH (CH3CH2)2NH (CH3CH2)sN (CH8CHa)2NH (CHsCH2)3N Products Isolated Yield, % 55 19 22 16 20 18 18 20 20 11 20 1 11 Ref.* 22 16 11 ^ > ES H-( O O 3 Ul W « d o H < > O 3
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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
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 215 and 216: CH3CH=CHCHO CH3(CHS)2CH=C(CH2CH3)CH
Page 217: (CHs)2C=CHCOCH3 (CH3)2C=CH(CH2)2COC
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 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
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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
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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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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
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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
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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
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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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