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Addends Crotonic acid (Cont'd) 1,3-Dimethylbutadiene Isoprene 1,1,3-Trimethylbutadiene Crotonolactone or AF'P-butenolide Butadiene TABLE V—Continued THE DIELS-AXDER ADDITION OF C^/S-UNSATURATED CARBONYL COMPOUNDS Products CH3 fY° 2l£ (See footnote 2) f (See footnote 2) CH3 CH* fSc02H (CH3) H3C^JCH3 (CO2H) (i) (ii) (See footnotes 2, 10) A 4 -TetrahydrophthaIide (See footnotes 2, 27) Ratio of Diene to Dienophile 1.8 1.0 1.0 0.5 — Solvent None None None None — — Temper ature, 0 C 180t. 150t. 18G1, 150t. HOt. 15O-190t. Time, hours 3 2-3 — 36 48 B.P.orM.P. 98 81-83 82-83 88.5-89 * — 88-92/ 1.5 mm. Yield, % — — 0 — References * 84 5 5 84 28 28 O H-I O > O H O GQ
2,3-Dimethylbutadiene Croio7toladonefy-methyl- 2,3-Dimethylbutadiene Cyclopentene-l-al 1,3,5-Hexatriene Diacetylethylene 2,3-Dimethylbutadiene l-Vinyl-6-methoxy- 3,4-dihydronaphthalene li2-Diacetyl'pro'pene-\ 2,3-Dimethylbutadiene 4,5-Dimethyl- AM^etrahydrophthalide 2,4,5-Trimethyl-A 4 -tetrahydrophthalide CH2 CHO 4,5-DIacetyl-1,2-dimethylcy elo hexene-1 ff^^COCH* Ii I ^^^-^s f^] COCH3 ^ A J COCH3 CH3okJk^J 4,5-Diaeetyl-l ,2,4-trimethyl eyelohexene-1 * References 69-116 are listed on pp. 172-173. t For table footnotes see pp. 134-135. — — 1.27 1.8 1.8 1.7 — —- Ethanol Benzene Benzene Benzene Benzene 15Ot. 15O-160t. 90-95 10Ot. 110-115t. 110-115t. 15Ot. 48 48 6 48 48 12 115-117/ 3.5 mm. 112-115/ 3.5 mm. 173-175 7 * 9 36-37 7 174-175 107-108 141/10 mm. — — — 25-30 23 28 28 14 98 99 99 98
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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
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: 1,1,3-Trimethylbutadiene 1,1,4-Tri
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
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1,3-Dimethylbutadiene 1,1,3-Trimet
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DIENE SYNTHESIS II 110 Diels and Al
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PREPARATION OF AMINES BY REDUCTIVE
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CH3CH=CHCHO CH3(CHS)2CH=C(CH2CH3)CH
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(CHs)2C=CHCOCH3 (CH3)2C=CH(CH2)2COC
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CH3COCH3 CH3COCH3 CH3COCH2CH3 CH3CO
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H2N (CH2) 2NH2 H2N(CH2)2NH2 H2N{CH2
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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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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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