Organic Reactions Volume 4 - Sciencemadness Dot Org

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Nitro Compound or Amine Used CH3(CH2)SNH2 (CH3)2CH(CH2)2NH2 (CH3)2CH(CH2)2NH2 Cyclohexylamine Cyelohexylamine Cyclohexylamine HO(CH2)2NH2 HO(CH2)2NH2 HO(CH2)2NH2 HO(CH2)2NH2 HO(CH2)2NH2 CH3CHOHCH2NH2 (CHa)2COHCH2NH2 CH3CHOHCH2C(CHS)2NH2 CH3CHOHCH2C(CH3)2NH2 CH3CHOHCH2C(CH3)2NH2 H2N(CHg)2NH2 H2N(CH2)2NH2 H2N(CH2)2NH2 H2N(CH2)2NH2 H«^(CH2)2NH2 TABLE X—Continued PEEPABATioN OF SECONDARY AMINES D. From Primary Amines or Nitro Compounds and Aldehydes—Continued Carbonyl Compound CH3(CH2)2CH0 CH3CHO (CH3)2C==CH(CH2)2C- (CH3)=CHCHO CH3(CH2)2CHO Arabinose Mannose CH3(CH2)2CH0 (CH3)2CHCHO CH3(CH2)sCHO CH3(CH2)5CHO CH3(CH2)3CH=C- (CH2CH3)CHO (CHs)2CHCH2CHO (CHs)2CHCH2CHO CH2O CH3CHO C6H5CHO CH3CH2CHO CH3(CH2)2CHO CH3(CH2)5CHO CH3 (CH2) sCH- (CH2CHs)CHO CH3(CH2)10CHO Reducing Agent H2 + Ni H2+Pt H2+ Pt H2 + Ni H2+Ni H2+ Pt H2+ Pt H2+Pt H2+ Pt H2+ Pt H2 +Pt H2+ Pt H2+ Pt — — H2 + Ni H2 + Ni H2 + Ni H2 + Ni H2 +Ni I Products Isolated [CH8(CH2)S]2NH [CHs(CH2)3]sN (CH3)2CH(CH2)2NHCH2CH3 CH3CH(CH3) (CH2)sCH(CH3) (CH2)*- NH(CHs)2CH(CHs)2 C6HuNH(CH2)sCHs C6H1INHCH2(CHOH)3CH2OH CeHiiNHCH2(CHOH)4CH2OH HO(CH2)2NH(CH2)3CHs HO(CH2)2NHCH2CH(CH3)2 HO(CH2)2NH(CH2)4CH3 HO(CH2)2NH(CH2)6CH3 HO (CH2)2NHCH2CH(CH2CH3) (CH2)4- CH3 CH3CHOHCH2NH(CH2)2CH(CH3)2 (CH3)2COHCH2NH(CH2)2CH(CHs)2 CH3COCH2C(CHS)2NHCH3 CH3COCH2C(CHs)2NHCH2CHs CH3COCH2C(CHS)2NHCH2C6H5 H2N(CH2)2NH(CH2)2CH3 H2N(CH2)2NH(CH2)3CHS CH3(CH2)3NH(CH2)2NH(CH2)sCHs H2N(CH2)2NH(CH2)6CH3 H2N(CH2)2NHCH2CH(CH2CH3)(CH2)g- CH3 H2N(CH2)2NH(CH2)nCH3 Yield, % 48 47 — 67 91 — —. 68 62 70 71 91 90 89 72-80 Quantitative — 42 59 13 — 60 61 Ref.* 16 18 18 23,24 11,25 11,25 26 26 26 26 26 59 60 135 136 136 137 137 137 137 137 to O Q > O H t—i O % CQ
H2N (CH2) 2NH2 H2N(CH2)2NH2 H2N{CH2)2NH2 H2N(CHg)5NH2 H2N(CHs)6NH2 H2N(CHs)6NH2 H2NC CCH3 O=J H2NC= NCH3 X / N C6H5 =CCH 3 O=C NCH3 C6H5 H2NC=CCH3 O=C NCH3 \ / N C6H5 H2NC=CCH3 o-A v NCH3 C6H5 * References 134-180 are listed on p. 255. CH3(CH2)7- CH=CH(CH2)7CHO C6H5CHO Furfural CH / \ CH CCHO Cl A A H V N CH2O CHs(CH2)2CHO (CH2O)3 CH3CHO CH3CH2CHO (CH3)2CHCHO H2+ Ni H2 + Ni H2+Ni H2+Ni H2+ Pt H2 + Ni H2+Pt H2+Pt H2 + Pt or H2+Co H2+ Pt H2N(CHS)2NH(CH2)ITCH8 H2N(CH2)2NHCH2C6H5 CeHgCH.jNH^H^NHCHgCeHs H2N(CHs)2NHCH2C4H3O CH / \ H2N(CH2)sNHCH2C CH CH CCl \ / N Mixture H2N(CHs)6NH(CHs)3CH3 CH3HNC=CCH3 I I O=C NCH3 v C6H5 CH3CH2HNC CCH3 O=C NCH3 CH3(CH2)2HNC-1-1.CCH3 o4 NCH3 N C6H5 (CHs)2CHCH2HNC=: =CCH3 O=C NCH3 \ / N C6H5 49 67 17 52 47 40 Almost quantitative 137 137 137 137 137 137 31 31 31 31 & m > > H H-I O O > HH Ul K< I O H Kj HH O to H-i
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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
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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 and 218: (CHs)2C=CHCOCH3 (CH3)2C=CH(CH2)2COC
Page 219: CH3COCH3 CH3COCH3 CH3COCH2CH3 CH3CO
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
Page 269 and 270: 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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