Organic Reactions Volume 4 - Sciencemadness Dot Org

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OO Addends Methyl acetyhnedicarboxylate (Confd) Stilbazole TABLE X—Continued THE DIELS-ALDER ADDITION OF ACETYLENIC DIENOPHELES TO HETEROCYCLIC DIENES CgHsCH=C Products f . N1N ~ WL/VJ2V-/£ls CH SO2Ca^JjCO2JCH, C6H5CH=CHI JL CO2CH3 CH3O2CS^JcO2CH, CO2CH, C6H5CH=C m CO2CHj ^NCO2CH, 3^J CO2CH* CO2CH8 Ratio of Diene to Dienophile Solvent Ether Ether Xylene Temperature, 0 C Room temp. Reflux Time, hours 72 B.P. or M.P. 187-188 205-206 192 Yield, % References * 116 116 116
2,3,4-Trimethylpyrrole H3Cp CCO2CH3 CHCO2CH3 (See footnote 10) 1.0 Benzene and petroleum ether 137-138 109 * References 69-116 are listed on pp. 172-173. 1 The primary addition product was not isolated, but was reduced without purification to the A^tetrahydro adduct. 2 During the reaction 230 ml. of carbon dioxide was collected. The theoretical amount is 350 ml. 3 During the reaction 1800 ml. of carbon dioxide was collected. The theoretical amount is 2700 ml. 4 The acid melts at 168°. 5 Saponification of the ester with hydrochloric acid at 100° effects a simultaneous decarboxylation, for the resulting acid agrees with the 3-hydroxy-5-methylbenzoic acid (m.p. 208°) of Bishop and Tingle (Dissertation, Munich, 1889). 6 During the reaction 580 ml. of carbon dioxide was evolved. The theoretical amount is 800 ml. 7 Trimellitic acid melts at 231°. 8 The tetramethyl l,8 n This reaction product (base : ester = 2:1) settles out of the reaction mixture; the second product is recovered from the mother liquors. * n It is the author's conclusion, although there is no evidence, that the higher-melting isomer is the trans form. Both isomers can be hydrogenated to the same dihydro adduct, identical with that from maleic anhydride and 2,3-dimethylpyrrole. 13 The crystals are brick-red. 14 These crystals are greenish yellow and have a greenish-yellow fluorescence. 15 The point of attachment of the dimethyl maleate residue to the methylim idazole nucleus has not been established. 16 The same product is obtained if the reaction mixture is allowed to stand 700 hours. 17 Yellowish-green crystals from methanol. 18 It is not possible to convert the labile adduct into the stable adduct by thermal means. This is the exception to the rule.
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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
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: OS Quinaldine Quinoline CX | JCH. j
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 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
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CH3NH2 CH3NH2 CH3NH2 CH3NH2 CH3NH2
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HO(CH2)2NH2 HO(CHa)2NH2 HO(CH2)2NH2
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(GHg)2COHCH2NH2 (CHs)2COHCH2NH2 CH3
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Amine, Nitro, Nitroso, or Azo Compo
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P-HOC6H4NH2 P-HOC6H4NH2 - P-HOC6H4N
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CeHgNHs C6H5NH2 C6HgNH2 C6H5NH2 P-C
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HN=C(CH3)CO2H CH2 SehifPs Base / \
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CH3CH2N=CHC6H5J CH3(CH2)2N=CHCH3f C
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C6HuN=CH(CH2)2CH3t C6Hi1N=CH(CH2)2C
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p-C6H5(CH2)2N=CHC6H40H f p-C6H5(CH2
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C6H5N-=CHCH2CH(CH3)2f C6H5N=CH(CHOH
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2,4'-CH3C6H4N=CHC6H4CIf 2,4 / -CH3C
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0-CH3OC6H4N=CH(CHOH)4CH2OH m-CH3OC6
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Amine Used CH3CH2NH2 Amine Used CH3
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Nitro Compound Used ^HOC6H4NO2 P-H2
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C6H5CHOHCH2CH(CH3)- NHCH3 C6H5CHOHC
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Amine Used (CHs)2NH (CHs)2NH (CH3)2
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C6H5NH(CHs)2CH3 C6H5NH(CHs)3CH3 C6H
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PREPARATION OF AMINES BY REDUCTIVE
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THE ACYLOINS 257 euphony and to avo
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THE ACYLOINS 259 A mechanism simila
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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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