Organic Reactions Volume 4 - Sciencemadness Dot Org

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404 ORGANIC REACTIONS Formula Ci7Hi6O4 Ci7HnON Ci7HIiO2N Ci7Hi9O2N Ci7Hi8ON2 Ci7H20ON2 Ci7H240N2 Ci8Hi4O Ci8Hi6O Ci8Hi8O CisH2oO Ci8H22O Ci8H28O Ci8Hi4O2 Ci8H22O2 Ci8H24O2 Ci8HuO3 Ci8H2o03 Ci8H22Og Ci8H26O3 CisHsoOa Ci8H3203 Ci8H84O3 CI8H22OB TABLE 11—Continued COMPOUNDS REDUCED BY THE WOLFF-KISHNER METHOD Compound 7-(p-Fhenoxybejru5oyl)-butyric acid 4-MethyI-l,2-benzo-3-azafluorenone4-Methoxy-l,2-benzo-3-a:aafluorenone0-(Tetrahydro-4-pyrariyl)cthyl 4'-quinolyl ketone 9-Rubanone Michler's ketone Michler's ketone 3,3',5,5'~Tetramethyl-4,4'~ diethylpyrroketono 2-Phenylaoctylnaphthalene 2-Keto-l,2,9,10,11,12-hexahydro-3,4-bonzophenanthrone 16-Equilenone 0-17-Equilenone 5-Keto-l,2,3,44etramethyl- 5,6,7,8-tetrahydroanthracene 2-Ketododecahydrochrysene Phenyl n-undecyl ketone p-Tolyl n-decyl ketone m-Diketohexahydrochrysene frans-Diketohexahydrochryseno Estrone Estrone Estrone Estrone Lumiestrone O-Methylpodocarpinal /3-(9-Phenanthroyl)propionic acid 7-Ketoestron© 2-Hydroxy»5-benzyloxyisoval» erophenone /S-(S or 6)Cyclohexane-l-spirohydrindoylpropionic acid 10-Keto-12-phenyl dodecanoio acid 12-Keto-13-(3-cyclopentcne)~ tridecylic acid 8-Keto-17~octadecenoic acid 8-Keto-16-octadecenoic acid Ethyl 5-keto-3-methyl-3amyldecanoate Diethyl a-acetyl-/S-(p-anisyl)glutaconate Normal Normal Product 4-Hydroxy-l,2-benzo-3-azafluorene Normal Normal Normal Normal 2,4-Dimethyl-3-ethylpyrrole Normal Normal ClS Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal 6-Hydroxypodocarpane Normal Normal None Normal Normal Normal Normal Normal None None * References 86a-413 are listed on pp. 416-422. t No alkaline catalyst was used. Method WD WDf WDf WS K WA WH WD WS WS WS WS WS WS •WD WD WH WH WS WS ? WS WS WS WS WS WA WS WD WD WD WD ? ? Yield 96A (er.) — 04A 8OB 63A __ 97B "•" 88A 22B (cr.) 53B (cr.) 76B 35A 40-50A — 34A 44A _ „ 35B _ 73B _ 51B 76B 48B — — 78A 7OA 65A (cr.) — 2 Reference* 40 255 28 256 257 20 2 258 259 260 261 261 262 263, 264 43 129 265 265 266 60 267 268 269 270 271 268 207 272 273 274 41 41 275 276
Formula Ci8H13ON Ci8H2IO3N Ci8Hi9O4N Ci9Hi2O Ci9H20O Ci9H22O Ci9H24O Ci9H28O C19H80O Ci9H20O2 Ci9H24O2 Ci9H28O2 Ci9Hs0O2 Cl9Hi603 Ci9Hi5ON Ci9H9O2N Ci9H25O3N THE WOLFF-KISHNER REDUCTION 405 TABLE II—Continued COMPOUNDS REDUCED BY THE WOLFF-KISHNER METHOD Compound 4-Ethyl~l,2-benzo-3-azafluorenone Metathebainone Hydroxycodeinone l,2-Benzanthracene-10-aldehyde3,4-B,enzo-l-phenanthraldehy4e 3,4-Benzo-2-phenanthral dehyde Chrysene-5-aldehyde Methyl /8-9-fluorenyl~/3-methylpropyl ketone l-Methyl-4-kcto-l,2,3,4-tetrahydro-7-sec-butylphenanthrene a-Bisdehydrodoisynolaldehyde /3-Bisdehydrodoisynolaldehyde 2-Keto-16-melhyldodecahydrochrysene-a A 16 -Androstene-3-one Androstanone Etiocholanone-17 A propeimin derivative Equilenin methyl ether 3-Keto-7-methoxy-2-methyl- 3,4,9,10,11,12-hexahydrocyclopentenophenanthrene Norcafostanedione Norcafestonal Androstane-3,17-dione Dehydroandrosterone Dehydroandrosterone Androstan-3 (/3)-ol-17-one /3-3-Phenanthroylisobutyric acid 4-Isopropyl-l,2-benzo-3-azafluorenone 2,3,5,6-Dibenzoylenepyridine Ketoazodehydroabietic acid C20Hi4O l-Acetyl-3,4-benzophenanthrene2-Acetyl-3,4-benzophenanthrene Normal Normal None Normal Normal Normal Ci9 Normal Normal Normal Normal Normal Normal Product Normal Normal Normal Normal Desoxoequilenin Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal Normal * References 86a-413 are listed on pp. 416-422. t No alkaline catalyst was used. C20 Method WDf WD WH WH WS WS WS WS ? WS WS WS WD WS WS WS WS WS WS WS WS WS WS WD WS WDf WDf WD WS WS Yield 56-63A 10OB 63B (cr.) 17B 49B _. _ — 53A 10OB 57B _ 61A 63B 79B Poor >80B 98A 16B 81A 98B (cr.) 81A __ — Reference* 255 277 278 232 262 279 280 281 251 281a 281a 264 282 283 283 284 285 264 286 287 286 288 289 290 291 28 230 292 - 279 379
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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
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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
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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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Page 359 and 360: SYNTHESIS OF BENZOQUINONES BY OXIDA
Page 369 and 370: ROSENMUND REDUCTION 363 For accompl
Page 371 and 372: ROSENMUND REDUCTION 365 acid in alm
Page 373 and 374: ROSENMUND REDUCTION 367 The Hydroge
Page 375 and 376: ROSENMUND REDUCTION 369 solution of
Page 377 and 378: ROSENMUND REDUCTION 371 TABLE I ALI
Page 379 and 380: Acid Chloride Benzoyl chloride p-Ca
Page 381 and 382: Acid Chloride 3-Furoic- 4~Carbometh
Page 383 and 384: ROSENMUND REDUCTION 377 106 Shoesmi
Page 385 and 386: THE WOLFF-KISHNER REDUCTION 379 INT
Page 387 and 388: THE W0LFF-KISHNER REDUCTION 381 mol
Page 389 and 390: THE WOLFF-KISHNER REDUCTION 383 dan
Page 391 and 392: THE WOLFF-KISHNER REDUCTION 385 Sod
Page 393 and 394: THE WOLFF-KISHNER REDUCTION 387 TAB
Page 395 and 396: THE WOLFF-KISHNER REDUCTION 389 Red
Page 397 and 398: THE WOLFF-KISHNER REDUCTION 391 Dir
Page 399 and 400: C7Hi2O C7H14O C7H0O2 C7H8O2 C7H6O4
Page 401 and 402: C9Hi0O C9Hi2O C9Hi4O Formula C9Hi6O
Page 403 and 404: Formula Ci0Hi6O CioHisO Ci0H6O2 Ci0
Page 405 and 406: Formula CnH16O CnHi8O CnHi6O2 CnHi8
Page 407 and 408: Formula Ci3H22O C13H10O3 Ci3Hi8O3 C
Page 409: Formula CI6HHO2 CI6HHO3 CI6H24O3 C1
Page 413 and 414: Formula C2IH34O C21H30O2 C21H32O2 C
Page 415 and 416: Formula C23H32O7 C23Hi7ON C24H3603
Page 417 and 418: Formula C25H40O7 C26Hi6O C26H44O C2
Page 419 and 420: Formula C29H46O C29H46O2 C29H48O3 C
Page 421 and 422: Formula C32H52O3 C32H46O4 C32H50O4
Page 423 and 424: THE WOLFF-KISHNER REDUCTION 417 133
Page 429 and 430: DEX Numbers in bold-face type r :ef
Page 431 and 432: Dialkylaminoquinonedisulfonates, 35
Page 433 and 434: 3-Methylpyrene, preparation by Wolf
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