Organic Reactions Volume 4 - Sciencemadness Dot Org

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300 ORGANIC REACTIONS Formula Ci0H8O4 Ci2Hi0O3 C12H10O8 Ci2Hi0O2N2 Ci4Hi2O2 Ci4Hi2O3 Ci4H12O4 Ci4Hi8O2 Ci4Hi8O8 Ci4H24O2 Ci4HiOO2Cl2 Ci4HiOO2Cl2 C14H10O2CI2 Ci4Hi0O2Br2 Ci4Hi0O2I2 Ci4Hi0O6N2 Ci4HIiO2Cl Ci4HiIO2Cl Ci4HnO2Br Ci4HnO2Br Ci4HnO2Br C14Hi4O2N2 Ci4H16O3N Ci5Hi2O4 Ci5H14O2 C15H14O2 Ci5Hi4O2 Furoin TABLE II BENZOINS PREPARED BY VARIOUS METHODS R'—CHOHCO—R Benzoin Benzfuroin (C6H6CHOHCOC4H3O) Benzfuroin (CCH6COCHOHC4H3O) 2-Pyridoin Benzoin 2'-Hydroxy- 2,2'-Dihydroxy- Cyclohexoylphenylcarbinol (C6H6CHOHCOC0Hii) l-(p-Anisyl)~2-cyclopentylothan-l-ol~ 2-one (4-Cn3OC6H4CHOHCOC6H9) Dodecahydro- CeHiiCHOHCOCoHn 2,2'~Dichloro- 3,3'-Dichloro~ 4,4'-Dichloro- 3,3'-Dibromo- 4,4'-Diiodo- 2,2'-Dinitro- 4-Chloro- 4'-Chloro- 3-Bromo- (?) 4-Bromo- 4'-Bromo- 4,4'-Diammo- 4-Dimethylammobenzfuroin [C4H8OCHOHCOC6H4N(CHa) 2-4] 3,4-Methylenedioxy- 2'-Methyl- 3-Melhyl- 4'-Methyl~ Method 1 5 1 4 1 1 5 3 4 6 t 4 t 4 4 O § 1 1 i 5 1 1 1 3 4 7 3 4 7 1 3 3 5 1 i 1 4 4 3 4 I * References 153-171 are listed on pp. 303-304. t The Grignard reagent added to carbon monoxide or nickel carbonyl. % By hydrolysis of 2,2'-fo's(methoxymethoxy)-benzoin. § From corresponding a-hydroxy acetaldehyde. M.P., 0 C 135 139 119 156 134 137 148 142-149 62-63 70-71 B.P. 140-141.5/ 3 mm. 62-63 56-57 88 85-87 123-124 122 155.5, 168-169 90-91 88-89 116 110-111 116-117 129-130 108-109 125-126 199 168 120 64-65 69.5-70 116 116-117 I Yield, % 38 86 92 93 90 33 45 70 80 26 12 20-40 91 8 35 17 94 84 32 93 32 70 57 30 32 15 50 24 J Reference* 48 94 19, 48, 54, 57 103 49 75, 154 52, 94, 162 95,96 103 111 151, 152 103 155 92 123 141 20, 104 33 156 52 33 157 44,45 96 104 71 96 104 71 53 96 96 119 53,54 19, 32, 53, 54,57 104 92 96 104
Formula CI5HHO2 CI6HHO3 CI6HHO3 CI5HHO3 CI5H14O3 Ci6H14O3 C15HHO6 CI5H20O3 C16Hi1O4Cl CI6HHO4CI Ci5HnO4Br Ci6HiSO3Cl Ci6H18O3Cl C16H13O3Cl C16H13O3Cl C15Hi3O3Br C16H12O4 C16Hi2O6 Ci6Hi405 Ci6Hi6O2 C16Hi6O2 C16Hi6O2 C16H16O3 C16H16O3 C16H16O4 C16Hi6O4 Ci6Hi6O4 Ci6Hi6O4 Ci6Hi6O4 Ci6Hi6O4 4-Methyl- 2-Methoxy- 2'~Methoxy- 4-Methoxy~ 4'-Metboxy- THE SYNTHESIS OF BENZOINS 301 TABLE II—Continued BENZOINS PREPARED BY VARIOUS METHODS R'—CHOHCO—R Benzoin 2-Hydroxy-5-methyl- 2'-Methoxy~2,4-dihydroxy- 4'-Methoxyphenyl hexahydrophenyl- (4-CH3OCCH4CHOHCOC6HII) 2 '-Chlor o-3,4-m ethylenedioxy- 4'-Chloro-3,4-meihylenedioxy- 3'-Bromo-3,4-methylenedioxy- 2'-Chloro-4-methoxy- 3'-Chloro~4~mol hoxy- 4'-Chloro-4-methoxy- 4-Chlor o-4 r -m ethoxy- 3'-Bromo-4-mothoxy (?)- 4,4'-Dialdehydo- 3,4,3',4'-Dimethylenodioxy- 4'-Meihoxy-3,4-methylenedioxy~ 2,2'-Dimethyl- 3,3'-Dimothyl- 4,4'-Dimethyl~ 2-Ethoxy- 2'-Ethoxy- 2,2'-Dimethoxy- 3,4-Dimethoxy (?)- 2',4-Dimethoxy- 3',3-Dimetnoxy- 3 '-4-Dimethoxy- 4,4'-Dimetlioxy- ^References 153-171 are listed on pp. 303-304. t The Hoesoh reaction. Method 3 4 1 1 4 1 2 4 7 2 3 4 7 7 t 4 1 1 1 1 I 4 7 7 i 1 1 5 1 1 1 1 5 4 4 1 1 1 4 1 1 4 1 5 M.P., 0 C 109- 110 56-57 78 58 105.5- 106.5 108 100 89 90 171 72-73 116 no 106 84 85.5 84.5- 85.5 70.5- 71.5 88 170-174 120 110 79 Oil 88-89 77-78 81-82 99-100 101.5 Oil 102 92-93 41-42 55 60 109-110 113 Yield, % 42- 47 70 25-45 94 50 48 41 74 50 40 33 60 25-30 20 85 70 20 80 87 90 16 14 55 79 20 70 5 60 62-90 Reference* 96 104 37 19 103 19, 54, 77 14, 59, 82, 86 90 71, 129 81, 84, 85 96 103, 105 71 130 149 123 18, 53, 54, 57 40, 76 53 76 91 91 72 72 76 158 51, 159 94 19 33 33 33, 160 52 104 104 35 36 19 103 20 161 108 39 52, 94, 162
Page 1 and 2:
Organic Reactions VOLUME IV EDITORI
Page 3 and 4:
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
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I-* SO N-ce-Dimethylindole 3,5-Dim
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Oi N-Methylindole a-Methylpyrrole N
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OS Quinaldine Quinoline CX | JCH. j
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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
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: PREPARATION OF AMINES BY REDUCTIVE
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: THE SYNTHESIS OF BENZOINS 299 C6HBC
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 339 and 340: SYNTHESIS OF BENZOQUINpNES BY OXIDA
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
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SYNTHESIS OF BENZOQUINONES BY OXIDA
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Page 363 and 364:
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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
Page 385 and 386:
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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