Weygand/Hilgetag Preparative Organic Chemistry

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582 Alteration of nitrogen groups in carbon-nitrogen compounds as nitroanilines, 4-ethoxy-2-nitroaniline, and aminoazobenzene can be similarly diazotized. 249b According to Hantzsch and Jochem 250 solid diazonium salts are prepared as follows: The amine hydrochloride is dissolved or suspended in a three-fold amount of glacial acetic acid and treated at 10° with the calculated amount of pentyl nitrite, with stirring; when all is dissolved, the mixture is treated cautiously with ether, which precipitates the diazonium salt. Solid benzenediazonium chloride: 251 Aniline hydrochloride (5 g) is suspended in a mixture of glacial acetic acid (30 ml) and dry, peroxide-free dioxan (30 ml). The suspension is cooled in an ice-salt bath, and ethyl nitrite is led in until all the solid has dissolved (an excess is detected by coloration of starch-iodide paper). Dry dioxan (150 ml) is then added in one portion, whereupon the benzenediazonium chloride separates as fine, white crystals. They are filtered off and washed twice with dioxan (25-ml portions). The "direct method": 2-Naphthalenediazonium chloride solution: 252 2-Naphthylamine (143 g, 1 mole) is added to a mixture of concentrated hydrochloric acid (450 ml) and water (500 ml). The resulting suspension of amine hydrochloride is cooled to 5° by addition of ice (500 g). Then solid sodium nitrite (ca. 69 g) is added, with vigorous stirring, until presence of a slight excess is indicated by a color on starch-iodide paper. Additional ice (ca. 600 g) is added gradually during the preceding reaction so that the temperature does not exceed 5°. At the end of the reaction small amounts of insoluble matter are filtered off. The "indirect method": Diazotization of sulfanilic acidi 24913 A solution of sodium sulfanilate (23 g) and sodium nitrite (7 g) in water (120 ml) is cooled to 0° and dropped with stirring into an ice-cold solution of concentrated sulfuric acid (17 ml) in water (100 ml). The diazonium salt separates instantaneously. Claus's method; general procedure: 2490 A solution of a weakly basic amine in hot glacial acetic acid (12 ml per gram of amine) is cooled rapidly to room temperature and treated gradually, with stirring, with a solution of sodium nitrite in sulfuric acid [7 ml of sulfuric acid (t/1.84) per gram of sodium nitrite]. The sulfuric acid solution of nitrite is prepared by adding finely powdered sodium nitrite to the acid with very vigorous stirring, warming the mixture to 70°, and, when dissolution is complete, cooling the solution to room temperature. An approximately 10% excess of sodium nitrite is used, calculated on the amine. A continuous process for the preparation of diazonium salts has been described by Hupfer. 253 The kinetics and mechanism of diazotization have been studied in depth (cf. Schmidt 254 ). Diazonium salts are unstable, both in the solid state and in solution. Solid diazonium salts should be handled only in small quantities and with very great caution as they decompose explosively with extreme violence on warming, on shock, or even without recognizable cause. 255 The nature'of the anion influences the liability to decomposition: chlorides and sulfates are generally less dangerous than nitrates or perchlorates. Diazonium solutions are not so dangerous, although they decompose slowly (often even if the temperature exceeds 5°); for reactions they are thus always freshly prepared. Methods for stabilizing diazonium salts have, however, been perfected in recent times; it is achieved by, e.g., salt formation with 1,5-naphthalenedisul- 249 (a) K. H. Saunders, "The Aromatic Diazo-Compounds and Their Technical Applications," E. Arnold & Co., 2 nd ed., 1949, pp. (b) 10, (c) 13, (d) 21. 250 A. Hantzsch and E. Jochem, Ber. Deut. Chem. Ges., 34, 3337 (1901). 251 W. Smith and C. E. Waring, /. Amer. Chem. Soc, 64, 469 (1942). 252 A. N. Nesmayanov, Org. Syn., Coll. Vol. II, 432 (1943). 253 H. Hupfer, Angew. Chem., 70, 244 (1958). 254 H. Schmidt, Chemiker-Ztg., 78, 565 (1954). 255 E. Bamberger, Ber. Deut. Chem. Ges., 28, 538 (1895).
Formation of the N-N bond by exchange 583 fonic acid or 2-hydroxynaphthalene-l-sulfonic acid, 256 by double-salt formation with mercury(n) chloride, 252 or by treatment of 2 moles of the diazonium salt with 1 mole of piperazine; 257 diazonium tetrafluoroborates have also often been used. 258 Diamino compounds can be tetrazotized. 249d Some ring substituents in the ortho-position to the newly formed diazonium group may cyclize with it, with or without elimination of nitrogen; for instance, 1,2,3-benzotriazole is obtained in 51% yield on diazotization of 0-phenylenediamine. 259 If the orthosubstituent is a methyl group an indazole is formed. 260 Two monographs deal in detail with the preparation, properties, reactions, and constitution of aromatic diazonium compounds. 249 * The diazotization of proteins has been described by Rohrlich. 261 4. Preparation of azides Particular care is required when working with azides as they are unusually treacherous explosives. The tendency of any one material to explode varies from batch to batch; and, if possible, no attempt should be made to isolate azides of low molecular weight. Storage of, and reactions involving, azides should be confined to solutions of less than 10% concentration. When working with volatile azides it is essential to avoid breathing the vapors; like hydrogen azide, organic azides have, inter alia, the property of expanding the blood vessels (similarity to alkyl nitrites; danger of circulatory collapse); azidoformic esters are especially active in this respect. Only those azide syntheses are treated below that involve formation of an N-N bond, namely: (i) by the action of ammonia on diazonium perbromides: 262 ArN2Br3 + NH3 > ArN3 + 3HBr (yield 55%) (ii) by reaction of hydrazines with nitrous acid: 263 ArNHNH2 + HONO > ArN3 + 2H2O (yield 65-68%) (iii) from diazo compounds and hydrazine hydrate: 264 ArN2X + H2NNH2 > H2O + ArN2—NHNH2 > ArN3 + NH3 (yield ca. 70%) (iv) from arenediazonium salts and O-alkylhydroxylamines: 265 ArN2Cl + RONH2 • ArN3 + ROH + HC1 (yield good) 256 N. Kornblum, Org. Reactions, 2, 285 (1944). 257 P. I. Drumm and co-workers, Sci. Proc. Roy. Dublin Soc, 22, 223 (1940). 258 G. Schiemann and W. Winkelmiiller, Org. Syn., Coll. Vol. II, 188,225 (1943); A. Wayne and co-workers, /. Amer. Chem. Soc, 64, 828 (1942). 259 R. E. Darmschroder and W. D. Peterson, Org. Syn., Coll. Vol. Ill, 106 (1955). 260 H. D. Porter and W. D. Peterson, Org. Syn., Coll. Vol. Ill, 660 (1955). 261 M. Rohrlich, Chemiker-Ztg., 80, 847 (1956). 262 K. Clusius and H. Hiirzeler, Helv. Chim. Acta, 37, 383 (1954). 263 R. O. Lindsay and C. F. H. Allen, Org. Syn., Coll. Vol. Ill, 710 (1955). 264 C. K. Banks and O. M. Gruhzit, /. Amer. Chem. Soc, 70, 1268 (1948). 265 A. B. Boese and co-workers, /. Amer. Chem. Soc, 53, 3530 (1931).
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PREPARATIVE ORGANIC CHEMISTRY
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WEYGAND/HILGETAG PREPARATIVE ORGANI
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Foreword to the 4 th Edition The fi
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Summary of Contents Introduction: O
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X Contents II. Addition of hydrogen
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x ii Contents II. Replacement of ha
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xiv Contents II. Esters 368 1. Repl
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xvi Contents 1. Replacement of nitr
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xviii Contents 5. Cleavage of the S
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xx Contents Chapter 11. Formation o
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xxii Contents 1.3. Formation of new
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xxiv Contents IV. Rearrangement of
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Introduction: Organization of the M
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PART A Reactions on the Intact Carb
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6 Formation of carbon-hydrogen bond
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8 Formation of carbon-hydrogen bond
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10 Formation of carbon-hydrogen bon
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86 Formation of carbon-deuterium bo
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100 Formation of carbon-deuterium b
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CHAPTER 3 Formation of Carbon-Halog
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104 Formation of carbon-halogen bon
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240 Formation of c arbon-halogen bo
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274 Formation of carbon-oxygen bond
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392 Cleavage of carbon-oxygen bonds
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CHAPTER 6 Formation of Carbon-Nitro
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406 Formation of carbon-nitrogen bo
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48 8 Formation of carbon-nitrogen b
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632 Formation of carbon-sulfur bond
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694 Formation of carbon-phosphorus
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CHAPTER 10 Formation of Metal-Carbo
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750 Formation of metal-carbon bonds
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7 52 Formation of metal-carbon bond
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814 Formation of carbon-carbon mult
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PARTB Formation of new carbon-carbo
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Addition to C=C bonds 847 Under the
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Addition to C= C bonds 849 A radica
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Addition to C=C bonds 851 ful catal
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formation (b) that is necessary for
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Addition to C —C bonds 855 Nitril
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Addition to C —C bonds 857 3,6-ep
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Addition to C—C bonds 8 59 Stereo
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Addition to C=C bonds 861 6. Additi
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Addition to C=C bonds 863 In this c
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Addition to C=C bonds 865 are added
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Addition to C=C bonds 867 amount of
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Addition to the C=O bond 869 Such a
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Addition to the C=O bond 871 Such c
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Addition to the C=O bond 873 3. For
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Addition to the C=O bond 875 In hyd
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Addition to the C=O bond 877 Finely
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Addition to the C=O bond 879 the te
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Addition to the C=O bond 881 A Grig
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Addition to the C=O bond 883 c. Tre
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Addition to the C= O bond 885 The d
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Addition to C-N multiple bonds 887
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C-C linkage by removal of hydrogen
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C~C linkage by removal of hydrogen
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C-C linkage by replacement of halog
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esters: 634 ' 640 ' 641 C-C linkage
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C-C linkage by replacement of hydro
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C-C linkage by replacement of OR by
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C-C linkage by replacement of O-acy
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C-C linkage by replacement of nitro
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tions (see also page 957): C-C link
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Removal of halogen with formation o
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Formation of a new C=C bond by remo
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Removal of sulfur with formation of
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Removal of phosphorus with formatio
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PART C Cleavage of Carbon-Carbon Bo
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Removal of carbon dioxide 1005 Only
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Removal of carbon dioxide 1007 resp
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Removal of carbon dioxide 1009 e. N
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Removal of carbon dioxide 1011 Hydr
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Removal of carbon d ioxide 1013 Thi
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Removal of carbon d ioxide 1015 as
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Removal of carbon dioxide 1017 char
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Removal of carbon monoxide 1021 Thi
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Removal of other fragments 1029 sol
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Removal of other fragments 1031 The
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Oxidative cleavage of carbon-carbon
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Hydrolytic cleavage 1047 Cleavage b
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PART D Rearrangements of Carbon Com
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Migration of a multiple bond 1057 A
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2 hours at 250-270°, thus: 54 Rear
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Rearrangement of halogen compounds
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Migration from oxygen to carbon 106
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Migration from nitrogen to carbon 1
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Migration from carbon to nitrogen 1
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Wagner-Meerwein rearrangement and r
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Cope rearrangement; valence isomeri
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Cope rearrangement; valence isomeri
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Rearrangement on decomposition of d
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Rearrangement on decomposition of d
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Appendix I Purification and drying
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Purification and drying of organic
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Preparation and purification of gas
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Preparation and purification of gas
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Preparative organic work with small
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SUBJECT INDEX This index deals prim
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Acetophenone, co-amino-, 451 —, b
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Amidic acids, 485 Amidines, 472 —
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Aporphine, 970 D-Arabinose, 1029
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Methane, diphenyltolyl-, 949 —, n
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Oxazole, 5-ethoxy-2-phenyl-, 858 Ox
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Propane, l,2,3-trichloro-2-methyl-,
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Valence isomerization, 1088 Valeral
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