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422 ORGANIC REACTIONS 382 Ruzicka and Marxer, HeIv. CMm. Ada, 25, 1561 (1942). 383 Kon and Soper, /. Chem. Soc, 1940, 1335. 884 Ruzicka, Rey, and Spillmann, HeLv. CMm. Acta, 25, 1375 (1942). 386 Ruzicka and Hausermann, HeIv. CMm. Acta, 25, 439 (1942). 386 Ruzicka, Jeger, Grob, and Hosli, HeIv. CMm. Acta, 26, 2283 (1943). 887 Jeger, Norymberski, and Ruzicka, HeIv. CMm. Acta, 27, 1532 (1944). 388 Jacobs and Fleck, J". Biol. Chem., 96, 341 (1932). 389 Harris and Noller, /. Am. Chem. Soc, 66, 1005 (1944). 890 Ruzicka, Grob, EgIi, and Jeger, HeIv. CMm. Acta, 26, 1218 (1943). 391 Elliott, Kon, and Soper, J. Chem. Soc, 1940, 612. 892 Ruzicka and Schellenberg, HeIv. CMm. Acta, 20, 1553 (1937). 393 Goodson, J. Chem. Soc, 1938, 999. 394 Ruzicka and Marxer, HeIv. CMm. Acta, 22, 195 (1939). 395 Ruzicka and Wirz, HeIv. CMm. Acta, 23, 132 (1940). 399 Ruzicka and Wirz, HeIv. CMm. Acta, 24, 248 (1941). 397 Ruzicka and Wirz, HeIv. CMm. Acta, 22, 948 (1939). 398 Ruzicka and Brenner, HeIv. CMm. Acta, 22, 1523 (1939). 399 Ruzicka, Jeger, Redel, and Volli, HeIv. CMm. Acta, 28, 199 (1945). 400 Ruzicka and Jegor, HeIv. CMm. Acta, 24, 1236 (1941). 401 Hoehn and Mason, J. Am. Chem. Soc, 62, 569 (1940). 402 Ruzicka and Giacomello, HeIv. CMm. Acta, 19, 1136 (1936). 403 Ruzicka and Jeger, HeIv. CMm. Acta, 25, 1409 (1942). 404 Fischer and Krauss, Ann., 521, 261 (1936). 405 Fischer, Moldenhauer, and Stts, Ann., 485, 1 (1931). 406 Fischor and Gibian, Ann,, 550, 208 (1942). 407 Fischer, Lakatos, and Schnell, Ann., 509, 201 (1934). 408 Conant, Dietz, and Werner, /. Am. Chem. Soc, 53, 4436 (1931). 409 Ruzicka and Marxer, HeIv. CMm. Acta, 23, 144 (1940). 410 Jeger, Nisoli, and Ruzicka, HeIv. CMm. Acta, 29, 1183 (1946). 411 Bilham and Kon, J. Chem. Soc, 1941, 552. 412 Fischer and Gibian, Ann,, 552, 153 (1942). 413 Fischer and Riedmair, Ann., 505, 87 (1933).
DEX Numbers in bold-face type r :efer to experimental procedures Abietic acid in Diels-Alder reaction, 26 1-Acenaphthaldehyde, preparation by Rosenmund reduction, 369 Acetoacetic ester condensation, Vol. I Acetylenedicarboxylic acid chloride, 84 Acetylenic acids in Diels-Alder reaction, 79-86 Acetylenic aldehydes in Diels-Alder reaction, 79 Acyloins, 256-268 cyclic, from esters of aliphatic dibasic acids, 262-263 from acetylenes, 265 from acid chlorides, 264 from aliphatic esters, 257-262, 267-268 application of the reaction, 260-262 experimental procedures, 267-268 mechanism of the reaction, 258-260 from allenes, 265 from 1,2-diketones, 266 from 1,2-glycols, 266 from glyoxals, 266 from a-halo ketones, 264-265 from a-hydroxy nitriles, 264 from nickel carbonyl, 264 photochemical and biological preparation, 266-267 tables, 260, 263, 268 Aldehydes, preparation by Rosenmund reduction, 362-377 Alder rules, 10 Aliphatic nitro compounds, use in reductive alkylation, 184, 192 Alkylation of aromatic compounds by Friedel-Crafts reaction, VoL III Alkylmercaptoquinones, 354 AHyI compounds in Diels-Alder reaction, 77-79 Aluminum alkoxides, reduction with, Vol. II Amination of heterocyclic bases by alkali amides, Vol. I Amines, oxidation to quinones, 317-318 preparation by reductive alkylation, 175-255 a-Aminobenzylphenylcarbinols, oxidation to ketones, 286 preparation by reduction of benzoin oximes, 285-286 a-Aminobenzyl phenyl ketones, conversion to benzoins, 286 preparation by oxidation of carbinols, 286 Aminophenols, oxidation to quinones, 318-321 preparation by coupling procedure, 318-319, 325 Aminoquinones, 351-352 Aniline black, 351 Anthracene-C403 adduct, 84 Anthracene derivatives in Diels-Alder reaction, 29 Anthraquinones, preparation via Diels- Alder reaction, 69 Arndt-Eistert reaction, Vol. I Aromatic nitro compounds, use in reductive alkylation, 187-189, 193-194 Aromatic nitroso compounds, use in reductive alkylation, 187-189 Arsinic and arsonic acids, preparation by Bart, Bechamp, and Rosenmund reactions, Vol. II Azines, formation from hydrazones, 380- 381 Azlactones, Vol. Ill Azo compounds, use in reductive alkylation, 187-188, 193-194 Benzils, reduction to benzoins, 291-293 2,3-Benzo-l-azafluorene, preparation by Wolff-Kishner reduction, 390 Benzoin, preparation by reduction of benzoic acid, 294 Benzoin condensation, 272-282
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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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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
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 and 410: Formula CI6HHO2 CI6HHO3 CI6H24O3 C1
Page 411 and 412: Formula Ci8H13ON Ci8H2IO3N Ci8Hi9O4
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 425 and 426: THE WOLFF-KISHNER REDUCTION 419 235
Page 427: THE WOLFF-KISHNER REDUCTION 421 331
Page 431 and 432: Dialkylaminoquinonedisulfonates, 35
Page 433 and 434: 3-Methylpyrene, preparation by Wolf
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