The organic chemistry of aliphatic nitrogen compounds:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Oxford u.a.
Clarendon Press
1994
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| Schriftenreihe: | The international series of monographs on chemistry
28 |
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XXVI, 767 S. graph. Darst. |
| ISBN: | 0198557833 |
Internformat
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| 100 | 1 | |a Brown, Ben R. |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a The organic chemistry of aliphatic nitrogen compounds |c B. R. Brown |
| 264 | 1 | |a Oxford u.a. |b Clarendon Press |c 1994 | |
| 300 | |a XXVI, 767 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 490 | 1 | |a The international series of monographs on chemistry |v 28 | |
| 650 | 7 | |a Azote - Composés organiques |2 ram | |
| 650 | 7 | |a Composés aliphatiques |2 ram | |
| 650 | 7 | |a Composés nitrés |2 ram | |
| 650 | 7 | |a Stikstofverbindingen |2 gtt | |
| 650 | 4 | |a Nitrogen compounds | |
| 650 | 0 | 7 | |a Stickstofforganische Verbindungen |0 (DE-588)4043811-9 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Aliphatische Verbindungen |0 (DE-588)4198956-9 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Stickstofforganische Verbindungen |0 (DE-588)4043811-9 |D s |
| 689 | 0 | 1 | |a Aliphatische Verbindungen |0 (DE-588)4198956-9 |D s |
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| 830 | 0 | |a The international series of monographs on chemistry |v 28 |w (DE-604)BV000005251 |9 28 | |
| 856 | 4 | 2 | |m GBV Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006485852&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
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Datensatz im Suchindex
| _version_ | 1804124152095834112 |
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| adam_text | THE ORGANIC CHEMISTRY OF ALIPHATIC NITROGEN COMPOUNDS B. R. BROWN
CLARENDON PRESS * OXFORD 1994 CONTENTS AMI 1.1 1.2 1.3 NES PREPARATION
1.1.1 1.1.2 1.1.3 1.1.4 1.1.5 1.1.6 1.1.7 1.1.8 NUCLEOPHILIC
SUBSTITUTION BY NITROGEN AT A SATURATED CARBON ATOM REDUCTION OF OTHER
NITROGEN-CONTAINING COMPOUNDS OTHER METHODS OF PREPARATION PREPARATION
OF CHIRAL AMINES PREPARATION OF 1, 2 DIAMINES PREPARATION OF ALLYLAMINES
PREPARATION OF A-AMINO KETONES INTERCONVERSIONS OF PRIMARY, SECONDARY,
AND TERTIARY AMINES AND QUATERNARY AMMONIUM SALTS PROTECTION OF THE
AMINO GROUP REACTIVITY 1.3.1 1.3.2 1.3.3 1.3.4 1.3.5 1.3.6 1.3.7 1.3.8
1.3.9 1.3.10 1.3.11 1.3.12 ENAMINES ENA 2.1 - 2.2 MINES BASICITY
NUCLEOPHILICITY OXIDATION ELIMINATION OF NITROGEN ACIDITY OF HYDROGEN
ATTACHED TO NITROGEN A -CARBON ATOM OF A QUATERNARY SALT AS AN
ELECTROPHILE A -CARBON OF AN AMINE AS A NUCLEOPHILE (UMPOLUNG) N,
A^-DIFLUORINATION ARYLATION JS-ALKYLAMINO-CARBONYL COMPOUNDS QUATERNARY
AMMONIUM SALTS AS PHASE TRANSFER CATALYSTS REDUCTIVE DEAMINATION TO
HYDROCARBONS AND YNAMINES PREPARATION 2.1.1 2.1.2 2.1.3 2.1.4 2.1.5
2.1.6 2.1.7 2.1.8 FROM ALDEHYDES OR KETONES FROM IMINIUM IONS FROM
CYANOALLENES FROM ALKYNES AND RELATED COMPOUNDS FROM YNAMINES FROM
FORMAMIDES FROM EPOXIDES FROM OXIMES REACTIVITY 2.2.1 2.2.2 2.2.3 2.2.4
2.2.5 REACTION WITH ELECTROPHILES ON NITROGEN OR ON THE P-CARBON ATOM
ACID HYDROLYSIS HYDROBORATION REACTION WITH TRICHLOROACETIC ACID
REDUCTION PAGE 1 2 2 8 18 29 31 32 35 36 45 47 47 47 57 62 63 66 67 69
69 70 70 70 79 79 80 80 83 84 84 86 87 87 88 89 89 89 90 91 92 VLLL
CONTENTS 2.2.6 REDUCTIVE CYCLIZATION 95 2.2.7 ALKYLATION 95 2.2.8
ACYLATION 98 2.2.9 ANNULATION 99 2.2.10 ARYLATION 99 2.2.11 PYRROLE
SYNTHESIS 100 2.2.12 CYCLOADDITION REACTIONS 102 2.2.13 OXIDATION 105
2.2.14 MICHAEL REACTION 106 2.2.15 A-ACETOXYLATION OF KETONES 109 2.2.16
OXYGENATION , 109 2.2.17 WITH TOSYL AZIDE 110 2.2.18 ALKENYNYLAMINE
SYNTHESIS 110 L-CHLORO-N,N-2-TRIMETHYLPROPENYLAMINE 110 2.3 PREPARATION
110 2.3.1 FROMANAMIDE 110 2.4 REACTIVITY 112 2.4.1 WITH ELECTRON RIEH
AROMATIC COMPOUNDS 112 2.4.2 WITH ALKENES AND ALKYNES 113 2.4.3 WITH
SCHIFF BASES 113 2.4.4 WITH MAGNESIUM 114 2.4.5 WITH ALLYLIC ALCOHOLS
114 YNAMINES 114 2.5 PREPARATION 115 2.5.1 FROM TRICHLOROENAMINES 115
2.5.2 FROM ALKYNE DERIVATIVES 116 2.5.3 FROM HALOETHENES 116 2.5.4 FROM
N, AF-DIALKYLPROP-2-YNYLAMINES 117 2.5.5 FROM A -HALOIMINIUM SALTS 117
2.5.6 FROM KETENE-S, N-ACETALS 117 2.5.7 FROM AMINES AND PHENYLACETYLENE
118 2.6 REACTIVITY 118 2.6.1 HYDROLYSIS 118 2.6.2 CYCLOADDITION
REACTIONS 118 3. IMINES 124 3.1 PREPARATION 125 3.1.1 BY CONDENSATION OF
ALDEHYDES OR KETONES WITH A PRIMARY AMINE 125 3.1.2 VIA A-EYANOAMINES
128 3.1.3 INTERCONVERSION OF IMINES BY EXCHANGE WITH AMINES 129 3.1.4
INTERCONVERSION OF IMINES BY EXCHANGE WITH CARBONYL COMPOUNDS 129 3.1.5
BY A WITTIG TYPE REACTION FROM AN IMINOPHOSPHORANE AND ANALDEHYDE 130
3.1.6 BY OXIDATION OF AMINES 130 3.1.7 FROM NITRILES AND GRIGNARD
REAGENTS 133 3.2 REACTIVITY 133 3.2.1 ELECTROPHILIC REACTIVITY OF CARBON
134 3.2.2 NUCLEOPHILIC REACTIVITY OF NITROGEN 140 3.2.3 ACIDITY OF THE
A-HYDROGEN ATOM 142 3.2.4 ISOMERIZATION REACTIONS 146 CONTENTS IX 3.2.5
REACTION AS ENAMINES 148 3.2.6 BIOCHEMICAL ROLE OF IMINES 151 IMINIUM
SALTS 161 3.3 PREPARATION 162 3.3.1 BY ALKYLATION OF IMINES 162 3.3.2 BY
THE REACTION OF MERCUROUS ACETATE ON TERTIARY AMINES 162 3.3.3 FROM THE
SALT OF A SECONDARY AMINE AND AN ALDEHYDE OR A KETONE 162 3.3.4 FROM
TERTIARY AMINES AND METHYLENE IODIDE*PREPARATION OF MANNICH REAGENTS 163
3.4 REACTIVITY 164 3.4.1 USE IN THE MANNICH REACTION 164 3.4.2 IN
DIELS-ALDER REACTIONS 164 3.4.3 WITH GRIGNARD REAGENTS OR ALKYL LITHIUMS
165 3.4.4 THE VILSMEIER REAGENT 165 3.4.5 REDUCTION BY SODIUM
CYANOBOROHYDRIDE 166 3.4.6 WITH A DIAZOALKANE*AN ALTERNATIVE TO THE
WITTIG REACTION FOR THE CONVERSION OF A KETONE INTO AN ALKENE 166 3.4.7
INTRODUCTION OF A CYANO GROUP INTO ACTIVATED AROMATICS USING VIEHE S
SALT 166 KETENIMINES 168 3.5 PREPARATION 168 3.5.1 FROM IMIDOYL
CHLORIDES 168 3.5.2 BY DEHYDRATION OF 7V-SUBSTITUTED AMIDES 169 3.5.3
FROM KETENES AND IMINOPHOSPHORANES 169 3.6 REACTIVITY 169 3.6.1
HYDROLYSIS 169 3.6.2 CYCLOADDITION REACTIONS 169 KETENIMINIUM SALTS 170
NITRILES (CYANIDES) 175 ALKYL NITRILES 175 4.1 PREPARATION 175 4.1.1 BY
SUBSTITUTION REACTIONS 175 4.1.2 BY ADDITION REACTIONS 178 4.1.3 BY
ELIMINATION OF WATER FROM AMIDES 183 4.1.4 BY ELIMINATION OF WATER FROM
OXIMES 184 4.1.5 BY OXIDATION OF PRIMARY AMINES 187 4.1.6 FROM ALDEHYDES
AND KETONES 188 4.1.7 VIA HYDRAZONES 191 4.1.8 FROM A-KETO ACIDS 195
4.1.9 FROMALCOHOLS 196 4.1.10 FROM CARBOXYLIC ACIDS 197 4.1.11 BY
ALKYLATION OFNITRILES 198 4.1.12 USE OF ORGANOBORANES 199 4.1.13 FROM
ZINC ALKYLS 200 4.1.14 BENZYLIC NITRILES 200 4.1.15 PREPARATION OF A,
/?-UNSATURATED NITRILES 200 4.1.16 TETRACYANOETHYLENE 208 4.1.17
GLYCIDIC NITRILES 209 4.1.18 PREPARATION OF /J-KETONITRILES 210 X
CONTENTS 4.1.19 PREPARATION OF CW-CYANOALDEHYDES 210 4.1.20 PREPARATION
OF A-CYANOETHERS 210 4.2 REACTIVITY 211 4.2.1 REACTION WITH
ELECTROPHILES ON NITROGEN 211 4.2.2 REACTION WITH NUCLEOPHILES ON CARBON
217 4.2.3 REDUCTION 225 4.2.4 REACTION WITH ORGANOMETALLIC REAGENTS 228
4.2.5 REACTIVITY OF A-HYDROGEN 229 4.2.6 CYCLOADDITION REACTIONS 239
ACYL NITRILES 242 4.3 PREPARATION 243 4.3.1 FROM ACYL HALIDES 243
4.3.2 FROM A, /?-UNSATURATED CYANOHYDRINS 244 4.4 REACTIVITY 244 4.4.1
WITH ALKENES 244 4.4.2 WITH DIENES 245 4.4.3 WITH SILYL ENOL ETHERS 245
CYANOTRIMETHYLSILANE 245 4.5 PREPARATION 245 4.5.1 FROM TRIMETHYLSILANE
245 4.6 REACTIVITY 246 4.6.1 WITH ACYL HALIDES 246 4.6.2 /?-AMINO
ALCOHOL SYNTHESIS 247 4.6.3 APPLICATION TO THE CONVERSION OF UNSATURATED
ALDEHYDES TO UNSATURATED KETONES 247 4.6.4 WITH KETALS AND ORTHOESTERS
249 4.6.5 PHENYLACETIC ACID PREPARATION 249 4.6.6 A-CHLORONITRILE
SYNTHESIS 249 4.6.7 A-ALKYLTHIONITRILE SYNTHESIS 250 USE OF OTHER
NITRILES IN SYNTHESIS 250 4.7 DI-IMINOSUCCINONITRILE 251 4.8
TRICHLOROMETHYLNITRILE 251 AF-OXIDES AND NITRONES 260 AF-OXIDES OF
TERTIARY AMINES 260 5.1 PREPARATION 260 5.1.1 FROM AMINES BY OXIDATION
260 5.1.2 BY DISTILLATION WITH DIMETHYLFORMAMIDE 261 5.2 REACTIVITY 261
5.2.1 DEOXYGENATION TO TERTIARY AMINES 261 5.2.2 AS OXIDIZING AGENTS 263
5.2.3 AS 1,3-DIPOLES 264 NITRONES 266 5.3 PREPARATION 266 5.3.1 BY
OXIDATION OF IMINES 266 5.3.2 FROM SILYL OXIMES 267 5.3.3 IN SITU
PREPARATION FROM SECONDARY AMINES 267 5.3.4 FROM ALDEHYDES OR KETONES
267 5.3.5 BY OXIDATION OF SECONDARY AMINES 267 CONTENTS XI 5.4
REACTIVITY 269 5.4.1 AS 1,3-DIPOLES 269 5.4.2 AS A NUCLEOPHILE 272
NITRILE N-OXIDES 273 5.5 GENERATION AND REACTION WITH ALKENES 273 ALKYL
ISONITRILES (ISOCYANIDES) 277 6.1 PREPARATION 277 6.1.1 FROM ALKYL
HALIDES 277 6.1.2 FROMAMINES 278 6.1.3 DEHYDRATION OFFORMAMIDES 279
6.1.4 FROM TERTIARY ALKENES 280 6.1.5 REDUCTION OF ISOCYANATES OR
URETHANES 281 6.2 REACTIVITY 281 6.2.1 REACTION ON CARBON WITH
ELECTROPHILES 282 6.2.2 CYCLIC ADDITION REACTIONS 286 6.2.3 REACTION ON
CARBON WITH POWERFUL NUCLEOPHILES 288 6.2.4 REDUCTION 291 VINYL
ISOCYANIDES 292 6.3 PREPARATION OF VINYL ISOCYANIDES 292 6.3.1 VIA
ISOCYANOMETHANE-PHOSPHORIC ACID DIETHYL ESTER 292 6.4 REACTIVITY OF
A-HYDROGEN ATOMS OF VINYL ISOCYANIDES 293 6.4.1 TOSYL METHYL ISONITRILE
293 CYANATES, ISOCYANATES, THIOCYANATES, AND ISOTHIOCYANATES 300 ALKYL
CYANATES 7.1 PREPARATION 7.1.1 7.1.2 FROM ALKOXIDES FROM ALKYL HALIDES
7.2 REACTIVITY ALKYL ISOCYANATES 7.3 PREPARATION 7.3.1 7.3.2 7.3.3 7.3.4
7.3.5 7.3.6 7.3.7 - 7.3.8 7.3.9 7.3.10 7.3.11 7.3.12 FROM METAL CYANATES
FROM PRIMARY AMINES BY OXIDATION OF ISONITRILES BY OXIDATION OF AN
ISONITRILE DICHLORIDE-FERRIC CHLORIDE COMPLEX FROM CARBAMATES FROM
METHYL THIOCARBAMATES FROM PYRIDINIUM OR PYRRILIUM SALTS FROM NITRILE
7V-OXIDES VIA THE CURTIUS REARRANGEMENT MODIFICATIONS OF THE CURTIUS
REACTION FROM AMIDES PREPARATION OF SUBSTITUTED ALKYL ISOCYANATES 7.4
REACTIVITY 7.4.1 7.4.2 7.4.3 7.4.4 HYDROLYSIS WITH ALCOHOLS WITH AMINES
WITH KETONES 300 300 300 300 301 301 301 301 301 302 303 303 304 305 305
306 306 307 308 309 309 309 310 311 XLL CONTENTS 7.4.5 WITH
ORGANOMETALLICS 7.4.6 OXIDATION 7.4.7 REDUCTION 7.4.8 DEOXYGENATION
7.4.9 WITH PHOSPHORAS YLIDES (WITTIG REACTION) 7.4.10 WITH BISULPHITE
IONS 7.4.11 CARBODIIMIDE FORMATION 7.4.12 POLYMERIZATION 7.4.13
FORMATION OF LACTAMS 7.4.14 WITHALKYNES ACYL ISOCYANATES 7.5 PREPARATION
7.5.1 FROM ACID CHLORIDES 7.5.2 FROM AMIDES CHLOROSULPHONYL ISOCYANATE
7.6 PREPARATION 7.7 REACTIVITY 7.7.1 WITH NUCLEOPHILIC AROMATIC
COMPOUNDS 7.7.2 WITH CARBOXYLIC ACIDS 7.7.3 WITH KETONES 7.7.4 WITH
ALKENES 7.7.5 WITH ALKYNES 7.7.6 FOR DEHYDRATION OF AMIDES THIOCYANATES
7.8 PREPARATION 7.8.1 FROM ALKYL HALIDES 7.8.2 FROM SULPHONATES 7.8.3
FROM SULPHENYL CHLORIDES 7.8.4 FROM AMINES 7.8.5 FROM /?-PROPIOLACTONES
7.8.6 FROM EPOXIDES 7.8.7 FROM HALOGENO-ORTHOCARBONIC ESTERS 7.9
REACTIVITY 7.9.1 HYDRATION 7.9.2 WITH ALCOHOLS 7.9.3 REDUCTION 7.9.4
ISOMERISM ISOTHIOCYANATES 7.10 PREPARATION 7.10.1 FROM AMINES 7.10.2
FROM ALKENES 7.10.3 FROM GLUCOSIDES 7.11 REACTIVITY 7.11.1 REDUCTION
7.11.2 WITH ALCOHOLS 311 312 313 313 314 314 314 315 315 315 316 316 316
316 317 317 317 317 318 318 318 319 320 320 320 320 321 321 322 322 322
323 323 323 324 324 325 325 325 325 326 327 327 327 327 8. AMIDES,
THIOAMIDES, AND CARBAMATES (URETHANES) 332 AMIDES 332 8.1 PREPARATION
333 8.1.1 FROM CARBOXYLIC ACID SALTS 333 CONTENTS XIII 8.1.2 FROM
CARBOXYLIC ACIDS AND AMINES 334 8.1.3 FROM CARBOXYLIC ESTERS AND AMINES
337 8.1.4 FROM ACYL CHLORIDES AND AMINES 340 8.1.5 FROMNITRILES 342
8.1.6 FROM THIOAMIDES 345 8.1.7 FROM A,J8-UNSATURATED ALDEHYDES 347
8.1.8 FROMALKENES 348 8.1.9 FROM ALCOHOLS AND NITRILES 349 8.1.10 FROM
ISOCYANATES 350 8.1.11 FROMKETONES 351 8.1.12 ACYLATION OF SECONDARY
AMIDES 353 8.1.13 ALKYLATION OF PRIMARY AMIDES F OR PREPARATION OF
SECONDARY AND TERTIARY AMIDES 353 8.1.14 FROM OXIMES BY THE BECKMANN
REARRANGEMENT 356 8.1.15 FROM N-PROTECTED PRIMARY AMINES 357 8.1.16 FROM
TERTIARY AMINES 357 8.1.17 FROM AZIDES AND CARBOXYLIC ACIDS 357 8.1.18
PREPARATION OF/3-KETOAMIDES FROM/3-DIKETONES 357 8.1.19 PREPARATION OF
JV-METHOXYAMIDES 359 8.2 REACTIVITY 359 8.2.1 REACTION WITH NUCLEOPHILES
360 8.2.2 REACTION WITH ELECTROPHILES 365 8.2.3 REACTION THROUGH THE
ENOL 366 8.2.4 ACIDITY OF HYDROGEN ATTACHED TO NITROGEN 367 8.2.5
ACIDITY OF A-HYDROGEN ATOMS 368 8.2.6 HYDROFORMYLATION AND
AMIDOCARBONYLATION 370 DIMETHYLFORMAMIDE (DMF) 371 8.3 AS A SOLVENT AND
AS A CATALYST 371 8.4 REACTIVITY 372 8.4.1 WITH ORGANOMETALLIC REAGENTS
372 8.4.2 WITH DIMETHYLSULPHATE 373 8.4.3 WITH ACID CHLORIDES 373 8.4.4
PREPARATION OF EPOXIDES 373 8.4.5 WITH ALCOHOLS AND BENZOYL CHLORIDE 376
8.4.6 SYNTHESIS OF AF, JV-DIMETHYLAMIDES 377 8.4.7 THE VILSMEIER
REACTION 377 ACETALS OF DIMETHYLFORMAMIDE 384 8.5 PREPARATION 384 8.6
REACTIVITY 385 8.6.1 WITH ACTIVE METHYLENE GROUPS 385 8.6.2 WITH
O-HYDROXYACETOPHENONE 385 8.6.3 PREPARATION OF A,/3-UNSATURATED KETONES
386 8.6.4 AS ALKYLATING REAGENTS 386 8.6.5 7RA/W-ACETALIZATION 387 8.6.6
WITH 1,2-DIOLS 388 8.6.7 REGIOSPECIFIC FORMATION OF MANNICH BASES 390
8.6.8 WITH SS-HYDROXYCARBOXYLIC ACIDS 391 THIOAMIDES 392 8.7 PREPARATION
392 8.7.1 FROMNITRILES 392 8.7.2 FROM AMIDES 393 CONTENTS CARBAMATES
(URETHANES) 393 8.8 PREPARATION 393 8.8.1 FROM PRIMARY AMINES 393 8.8.2
FROM SECONDARY AMINES 393 8.8.3 FROM PRIMARY OR SECONDARY AMINES 394
8.8.4 FROM SECONDARY ALCOHOLS AND ISOCYANATES 395 8.8.5 FROM CARBOXYLIC
ACIDS 395 8.8.6 PREPARATION OF ALLYLIC URETHANES 395 8.9 REACTIVITY 396
8.9.1 DEGRADATION TO AMINES - 396 8.9.2 GENERATION OF A NITRENE 397
8.9.3 CYCLIZATION 398 DITHIOCARBAMATES 399 SULPHONAMIDES 399 UREAS,
THIOUREAS, AND CARBODIIMIDES 406 UREAS AND THIOUREAS 406 9.1 PREPARATION
407 9.1.1 FROM CYANIC ACID OR ISOCYANATES 407 9.1.2 BY THE CURTIUS,
LOSSEN, AND SCHMIDT REACTIONS 407 9.1.3 BY OXIDATION OF A PRIMARY AMIDE
408 9.1.4 PREPARATION OF SUBSTITUTED UREAS 408 9.1.5 FROM AMINES 409
9.1.6 FROM THIOUREAS AND THIOAMIDES 411 9.1.7 PREPARATION OF THIOUREAS
411 9.2 REACTIVITY 412 9.2.1 PROTONATION AND ALKYLATION 412 9.2.2 NORMAL
AMIDE REACTIONS 413 9.2.3 REACTIONS THROUGH DECOMPOSITION TO ISOCYANATES
413 9.2.4 WITH SS-DICARBONYL COMPOUNDS TO GIVE PYRIMIDINES 414 9.2.5 WITH
(-)-EPHEDRINE HYDROCHLORIDE 414 CARBODIIMIDES 415 9.3 PREPARATION 415
9.3.1 FROM 1,3-DISUBSTITUTED UREAS AND THIOUREAS 415 9.3.2 FROM
ISOCYANATES 416 9.3.3 FROM THIOUREAS 416 9.4 REACTIVITY 416 AMIDINES 421
10.1 PREPARATION 422 10.1.1 THE PINNER SYNTHESIS 422 10.1.2 DIRECT
REACTION OF AMMONIA WITH NITRILES 422 10.1.3 FROM A NITRILE, AN ALKYL
HALIDE, AND AN AMINE 423 10.1.4 FROM AN ISONITRILE AND AN AMINE 424
10.1.5 THE ACTION OF HMPT ON SECONDARY AMIDES 424 10.1.6 PREPARATION OF
DICHLOROAMIDINES 424 10.1.7 AMIDINE SALTS FROM DMF AND THIONYL CHLORIDE
AND THEIR USES 425 10.1.8 FROM ACIDS AND AMINES 426 10.1.9 FROM CYANURIC
CHLORIDE, DMF, AND AMINES 426 10.2 REACTIVITY 426 10.2.1 SYNTHESIS OF
PYRIMIDINES AND IMIDAZOLES 426 CONTENTS XV 10.2.2 REACTION WITH
HYDRAZINE AND SYNTHESIS OF 1,2,4-TRIAZINES 427 10.2.3 DBUANDDBN 428
10.2.4 GUANIDINES 430 NITROALKANES AND NITROALKENES 433 NITROALKANES 433
11.1 PREPARATION 434 11.1.1 FROM ALKYL HALIDES AND METAL NITRITES 434
11.1.2 BY ADDITION OF DINITROGEN TETROXIDE TO ALKENES 435 11.1.3 BY
OXIDATION OF PRIMARY AMINES 436 11.1.4 BY OXIDATION OF OXIMES 437 11.1.5
FROM CARBOXYLIC ACIDS 439 11.1.6 FROM ACYL NITRATES 440 11.1.7 FROM
ISOCYANATES 440 11.1.8 FROMAZIDES 440 11.1.9 FROM NITROALKENES 441
11.1.10 A -NITRO ESTERS 442 11.1.11 A-NITROCYCLOHEXANONES 442 11.1.12
NITROFLUOROCOMPOUNDS 443 11.2 REACTIVITY 443 11.2.1 ACIDITY OF
A-HYDROGEN ATOMS 443 11.2.2 REACTION WITH ELECTROPHILES 452 11.2.3
REACTIONS OF THE NITRO GROUP WITH NUCLEOPHILES 461 NITROALKENES AND
NITROALKYNES 470 11.3 PREPARATION 470 11.3.1 HENRY REACTION (FROM
CARBONYL COMPOUNDS) 470 11.3.2 FROM ALDEHYDES AND KETONES 471 11.3.3
FROM ALKENES 471 11.3.4 FROM NITROALKANES 474 11.3.5 FROM CYCLIC NITRO
KETONES 475 11.3.6 BY PYROLYSIS OF NITRO-SUBSTITUTED MANNICH BASES 475
11.3.7 PREPARATION OF 1-NITRO-1,3-DIENES 475 11.4 REACTIVITY 478 11.4.1
REDUCTION TO ALKENES 478 11.4.2 CONVERSION TO ALDEHYDES AND KETONES 478
11.4.3 MICHAEL ADDITION 479 11.4.4 DIELS-ALDER REACTIONS 479 11.4.5
CONVERSION INTO ALLYLIC ALCOHOLS 481 11.4.6 USEINPREPARATION OF AROMATIC
KETONES 482 11.4.7 CONVERSION INTO DITHIOACETALS 483 11.4.8 REDUCTION TO
ALKOXYOXIMES 484 ALLYLIC NITRO COMPOUNDS 484 11.5 REACTIVITY 484 11.5.1
REDUCTION TO ALKENES 484 11.5.2 CONVERSION TO ALLYLIC PHENYL SULPHONES
484 11.5.3 ALLYLIC ALKYLATION 485 11.5.4 CONVERSION TO ALLYLIC
THIOETHERS 486 NITROSOALKANES AND ALKENES 486 11.6 PREPARATION 486
11.6.1 FROM ALKYLHYDROXYLAMINES 486 CONTENTS 11.6.2 FROM SS-CHLORO-OXIMES
487 11.6.3 FROM A-CHLOROKETONES 487 11.7 REACTIVITY 488 11.7.1 WITH
TRIALKYLPHOSPHITES 488 N-NITROSO COMPOUNDS: NITROSAMINES, NITROSAMIDES,
NITROSOUREAS, AND NITROSOURETHANES 494 NITROSAMINES 494 12.1
NITROSAMINES DERIVED FROM PRIMARY AMINES 494 12.2 NITROSAMINES DERIVED
FROM SECONDARY AMINES 495 12.3 PREPARATION 496 12.3.1 FROM SECONDARY
AMINES 496 12.3.2 FROM TERTIARY AMINES 501 12.3.3 FROM PRIMARY AMINES
502 12.4 REACTIVITY 503 12.4.1 DECOMPOSITION BY ACIDS 503 12.4.2 WITH
TRANSITION METAL CARBONYL COMPLEXES 504 12.4.3 REACTION WITH
NUCLEOPHILIC ORGANOMETALLIC REAGENTS 504 12.4.4 REACTION WITH BASES 506
12.4.5 WITH REDUCING AGENTS 509 12.4.6 REACTION WITH OXIDIZING AGENTS
510 12.4.7 REACTION WITH ARYL HALIDES 510 12.4.8 DEOXYGENATION 510
12.4.9 PHOTOCHEMICAL REACTIONS 511 12.4.10 REACTIONS WITH RADICALS 512
12.4.11 OVERBERGER-LOMBARDINO REACTION 512 NITROSAMIDES 512 12.5
PREPARATION 513 12.6 REACTIVITY 513 NITROSOUREAS AND NITROSOURETHANES
514 DIAZOALKANES 517 13.1 PREPARATION 517 13.1.1 BYTHEACTIONOFALKALI 517
13.1.2 PREPARATION OF DIAZOMETHANE FROM CHLOROFORM AND HYDRAZINE 519
13.1.3 FROM PRIMARY AMINES WITH AN ELECTRON-ATTRACTING GROUP ON THE
A-CARBON ATOM 520 13.1.4 FROM HYDRAZONES 520 13.1.5 BY DIAZO TRANSFER
521 13.1.6 THE FORSTER SYNTHESIS 522 13.1.7 PREPARATION OF DIAZOKETONES
FROM DIAZOMETHANE AND ACYL CHLORIDES 522 13.1.8 PREPARATION OF
SUBSTITUTED DIAZOKETONES 523 13.2 REACTIVITY 524 13.2.1 AS A NUCLEOPHILE
OR AS A BASE 524 13.2.2 AS AN ELECTROPHILE 529 13.2.3 AS A SOURCE OF
CARBENES 530 13.2.4 CYCLOADDITIONS OF DIAZOALKANES ACTING AS 1,3-DIPOLES
532 CONTENTS XVN DIAZOALKANES CONTAINING OTHER FUNCTIONAL GROUPS 536
13.3 REACTIVITY 536 13.3.1 WOLFF REARRANGEMENT OF DIAZOKETONES 536
13.3.2 RHODIUM CATALYSED DECOMPOSITION OF DIAZOESTERS AND DIAZOKETONES
536 13.3.3 SYNTHESIS OF KETONES 537 13.3.4 SYNTHESIS OF
A-HALO-A,/3-UNSATURATED KETONES 538 13.3.5 SYNTHESIS OF SS-DIKETONES 538
13.3.6 FORMATION OF CYCLIC SYSTEMS 538 13.3.7 DIAZOACETYL CHLORIDE FOR
THE FORMATION OF ESTER OR AMIDE DERIVATIVES 539 13.3.8
TRIMETHYLSILYLDIAZOMETHANE 540 13.3.9 DIMETHYL DIAZOMALONATE 543 13.3.10
DARZEN S REACTION ON A-HALOGENODIAZOKETONES 544 13.3.11
A,/J-EPOXYDIAZOMETHYL KETONES 544 14. HYDROXYLAMINES 550 OXIMES AND
0-ALKYLOXIMES 550 14.1 PREPARATION 551 14.1.1 FROM HYDROXYLAMINE AND
ALDEHYDES OR KETONES 551 14.1.2 BY THE ACTION OF NITROUS ACID ON
REACTIVE METHYLENE GROUPS 551 14.1.3 BY REDUCTION OF ALLYLIC NITRO
COMPOUNDS WITH CARBON DISULPHIDE 552 14.1.4 FROM STYRENES BY REACTION
WITH ETHYL NITRITE 552 14.2 REACTIVITY 552 14.2.1 REDUCTION 552 14.2.2
REACTIVITY TOWARDS NUCLEOPHILES ON CARBON 554 14.2.3 CONVERSION TO
ALDEHYDES AND KETONES 555 14.2.4 THE BECKMANN REARRANGEMENT 557 14.2.5
VARIANTS OF THE BECKMANN REARRANGEMENT 558 14.2.6 O-ALKYLOXIMES IN
RADICAL REACTIONS 560 14.2.7 CLEAVAGE 562 14.2.8 ALDOXIMES UNDER
BECKMANN CONDITIONS 564 14.2.9 REDUCTION OF O-ALKYLBENZALDOXIMES 564
14.2.10 CONVERSION OF OXIMES INTO ENAMIDES AND ENIMIDES 564 14.2.11
SYNTHESIS OF BENZOFURANS 567 14.2.12 SYNTHESIS OFPYRROLES 568 14.2.13
ALKYLATIONOFJS-DIKETONES 569 14.2.14 1,3-DIPOLAR ADDITION OF SILYL
OXIMES WITH ALKENES AND ALKYNES 569 14.2.15 REACTION OF
O-METHYLALDOXIMES WITH GRIGNARD REAGENTS 570 JV-ALKYLHYDROXYLAMINES 570
14.3 PREPARATION OF ./V-MONOALKYLHYDROXYLAMINES 570 14.3.1 FROM
NITROALKANES AND NITROALKENES 570 14.3.2 FROM OXIMES 572 14.3.3
FROMAMINES 572 14.3.4 FROMAMIDES 573 14.4 REACTIVITY 573 14.4.1
SYNTHESIS OF IMIDAZOLES 573 14.4.2 WITH ALLYL ESTERS 575 14.4.3
SYNTHESIS OF A TRICYCLIC SYSTEM 575 CONTENTS 7V,IV-DIALKYLHYDROXYLAMINES
576 14.5 PREPARATION 576 14.5.1 BY ALKYLATION OF HYDROXYLAMINE 5 76
14.5.2 BYREDUCTION 576 14.5.3 BY OXIDATION OF SECONDARY AMINES 577
14.5.4 BY PYROLYSIS OF AMINO N-OXIDES 579 0-ALKYLHYDROXYLAMINES 579
14.6 PREPARATION 579 14.6.1 BY GABRIEL TYPE REACTION 579 14.7 REACTIVITY
581 14.7.1 SYNTHESIS OF 2,3-DISUBSTITUTED PYRIDINES 581 14.7.2 SYNTHESIS
OF 1,3-AMINO ALCOHOLS FROM O-BENZYLHYDROXYLAMINE 581
/Y,0-DIALKYLHYDROXYLAMINES 581 14.8 PREPARATION 581 14.8.1 BY REDUCTION
OF O-ALKYLOXIMES 581 14.8.2 BY REDUCTION OF O-ACYLOXIMES 582 14.9
REACTIVITY 583 14.9.1 FORMATION OF ALDEHYDES AND KETONES 583
N-ACYLHYDROXYLAMINES (HYDROXAMIC ACIDS) 584 HYDRAZINES 588 ALKYL
HYDRAZINES (1) AND (2) 588 15.1 PREPARATION 588 15.1.1 FROM ALKYL
HALIDES 588 15.1.2 FROM MONOALKYL UREAS 588 15.1.3 FROM HYDRAZONES 589
15.2 REACTIVITY 590 15.2.1 ALKYLATION 590 15.2.2
A^TV -DIISOPROPYLHYDRAZINE FOR PROTECTION OF CARBOXYLIC ACIDS 590 15.2.3
AR,7V -DIMETHYLHYDRAZINE 591 ACYL HYDRAZINES (3) 592 15.3 PREPARATION
592 15.3.1 FROM ACYL HALIDES AND HYDRAZINE 592 15.3.2 FROM CARBOXYLIC
ACIDS AND TOSYL HYDRAZINE 593 15.3.3 FROM CARBOXYLIC ACIDS AND ALKYL
HYDRAZINES 593 15.4 REACTIVITY 593 15.4.1 REDUCTION TO HYDROCARBONS 593
15.4.2 OXIDATION 595 15.4.3 OXIDATIVE CLEAVAGE WITH LEAD TETRAACETATE
596 HYDRAZINIUM SALTS 597 15.5 PREPARATION 597 15.5.1 FROM
O-MESITYLENESULPHONYLHYDROXYLAMINE 597 HYDRAZONES (5) 598 15.6
PREPARATION 598 15.6.1 FROM ALDEHYDES OR KETONES 598 15.6.2 FROM
DIAZONIUM SALTS 598 15.6.3 THE JAPP-KLINGEMANN REACTION 599 CONTENTS XIX
15.7 REACTIVITY 600 15.7.1 WITH IODINE OR PHSEBR AND BASE 600 15.7.2
CLEAVAGEOF 7V,./V -DIMETHYLHYDRAZONES 600 15.7.3 THE DIELS-ALDER
REACTION 601 15.7.4 OXIDATION TO ALKYNES 601 15.7.5 OXIDATION TO
AZOALKENES 602 15.7.6 REGENERATION OF CARBONYL COMPOUNDS FROM
2,4-DINITROPHENYLHYDRAZONES 603 15.7.7 WITH IODINE 603 15.7.8 WITH
EPOXIDE AND BASE 603 15.7.9 OSAZONES 603 15.7.10 WOLFF-KISHNER AND
HUANG-MINLON REACTIONS 604 TOSYL HYDRAZONES 605 15.8 REACTIVITY 606
15.8.1 WITH MONOSACCHARIDES 606 15.8.2 REDUCTION 606 15.8.3 SYNTHESIS OF
ALKENES 606 R-BUTYL HYDRAZONES 608 15.9 SYNTHESIS OF KETONES OR
A-HYDROXYKETONES 608 SULPHONYL HYDRAZONES 608 15.10 GENERATION OF VINYL
LITHIUM REAGENTS 608 DIIMIDE 609 16. AZO AND AZOXY COMPOUNDS 615 615 615
615 619 620 621 621 623 624 624 625 626 626 627 628 628
AZOBISISOBUTYRONITRILE (AIBN) 630 16.3 REACTIVITY 630 16.3.1
HALOGENATION OF HYDROCARBONS 631 16.3.2 DEHALOGENATION 631 16.3.3
REDUCTION 632 ELECTROPHILIC AZO COMPOUNDS 632 16.4 REACTIVITY 632 16.4.1
ELECTROPHILIC SUBSTITUTION REACTIONS 632 16.4.2 SYNTHESIS OF
CARBODIIMIDES 633 16.1 PREPARATION 16.1.1 16.1.2 16.1.3 16.1.4 16.1.5
16.1.6 16.1.7 OXIDATION OF 1,2-DIALKYLHYDRAZINES OXIDATIVE COUPLING OF
AMINES OXIDATION OF UREAS FROM HYDRAZODICARBOXYLATE ESTERS FROM AZINES
OXIDATION OF AF,JV -DIALKYLSULPHAMIDES THERMAL ISOMERIZATION 16.2
REACTIVITY 16.2.1 16.2.2 16.2.3 16.2.4 16.2.5 16.2.6 TAUTOMERISM AND
BASICITY OXIDATION REDUCTION SYNTHESIS OF THREE-MEMBERED RINGS FORMATION
OF EPOXIDES FROM AZO ACETATES USE OF AZODICARBONYL COMPOUNDS CONTENTS
16.4.3 WITHSILANES 633 16.4.4 HYDROBORATION 634 AZOXY COMPOUNDS 634 16.5
PREPARATION 634 16.5.1 OXIDATION OF AZO COMPOUNDS 634 16.5.2 REDUCTION
OF AZODIOXY COMPOUNDS 635 16.5.3 CONDENSATION OF NITROSO COMPOUNDS 635
16.5.4 OXIDATION OF HYDROXYLAMINES 636 16.5.5 ALKYLATION OF DIAZOTATES
636 16.6 REACTIVITY , 637 16.6.1 BASICITY 637 16.6.2 REARRANGEMENT 638
16.6.3 REDUCTION TO AZO COMPOUNDS 638 16.6.4 REDUCTION TO HYDRAZO
COMPOUNDS 639 16.6.5 REDUCTIVE CLEAVAGE 639 16.6.6 PHOTOCHEMICAL
ISOMERISM 639 AZIDES 644 ALKYL AZIDES 644 17.1 PREPARATION 644 17.1.1 BY
THE USE OF THE AZIDE ION IN SN REACTIONS 644 17.1.2 FROM DIAZOALKANES
647 17.1.3 FROM ALDEHYDES AND KETONES 648 17.1.4 FROM GRIGNARD REAGENTS
OR LITHIUM DERIVATIVES OF PRIMARY AMINES BY DIAZO TRANSFER 648 17.1.5 BY
ADDITION TO ALKENES 649 17.1.6 ALKYLARYL AZIDES 651 17.1.7 BY AZIDE
TRANSFER 651 17.1.8 A-AZIDOETHERS 653 17.2 REACTIVITY 653 17.2.1 WITH
NUCLEOPHILES 653 17.2.2 WITH ELECTROPHILES 659 17.2.3
1,3-DIPOLARADDITIONS 663 17.2.4 NITRENES 664 17.2.5 CYCLIZATION WITH
BORON TRICHLORIDE 666 17.2.6 AZA-WITTIG REACTION 666 17.2.7
INTRAMOLECULAR CYCLIZATION OF VINYL AZIDES 667 17.2.8 REARRANGEMENT TO
IMINES 667 ACYL AZIDES 668 17.3 PREPARATION 668 17.3.1 BY NITROSATION OF
ACYL HYDRAZINES 668 17.3.2 FROM ACYL CHLORIDES 668 17.3.3 FROM
CARBOXYLIC ACIDS 669 17.4 REACTIVITY 670 17.4.1 REARRANGEMENTS (CURTIUS
AND SCHMIDT) 670 17.4.2 DECOMPOSITION TO AN ALDEHYDE OR KETONE AND A
NITRILE 671 ALKYL NITRITES AND NITRATES 675 ALKYL NITRITES 675 18.1
PREPARATION 675 18.1.1 FROMALCOHOLS 675 CONTENTS XXI 18.2 REACTIVITY 675
18.2.1 AS A SUBSTITUTE FOR NITROUS ACID 675 18.2.2 A-NITROSATION OF
KETONES 676 18.2.3 USE IN THE PROTECTION OF AMINO ACIDS (AS BOC) 676
18.2.4 OXIDATION OF DISUBSTITUTED PHENOLS 677 ALKYL NITRATES 678 18.3
PREPARATION 678 18.3.1 FROMALCOHOLS 678 18.3.2 FROMAMINES 678 18.3.3
FROM ALKYL HALIDES 678 18.4 REACTIVITY 679 18.4.1 WITH NITRILES 679
18.4.2 VASODILATION 680 19. NITRAMINES 682 19.1 PREPARATION 682 19.1.1
FROM CARBAMATES 682 19.1.2 BY NITRATION OF ACYL DERIVATIVES OF SECONDARY
AMINES 683 19.1.3 NITRATION OF SECONDARY AMINES 683 19.1.4 OXIDATION OF
NITROSAMINES 683 19.1.5 POLYNITRATION OF HEXAMETHYLENE TETRAMINE 683
19.1.6 PREPARATION OF N-NITROAMIDES 684 19.2 REACTIVITY 684 19.2.1
ACIDITY 684 19.2.2 REDUCTION 685 20. SS-AUINO ALCOHOLS 686 20.1
PREPARATION 686 20.1.1 FROMEPOXIDES 686 20.1.2 FROM SILYL ENOL ETHERS
687 20.1.3 USING ORGANOMETALLICS 687 20.1.4 FROM NITROALKANES BY
REACTION WITH ALDEHYDES OR KETONES 689 20.1.5 FROM NITROALKENES 690
20.1.6 FROM A -AMINO ACIDS 691 20.1.7 FROM ETHYL ESTERS OF A-AMINO ACIDS
692 20.1.8 FROM SS-HYDROXY AMIDES 692 20.1.9 FROMALKENES 693 20.1.10
FROMOXIMES 694 20.1.11 FRORRURANS-L,2-BROMOHYDRINS 694 20.1.12 FROM
ALLYLIC ALCOHOLS 695 20.1.13 FROMIMINES 695 20.1.14 STEREOSELECTIVE
SYNTHESES 697 20.2 REACTIVITY 697 20.2.1 WITH CARBONYL COMPOUNDS 697
20.2.2 ALKALINE HYDROLYSIS OF 7V-CHLORO-/?-AMINO ALCOHOLS 701 20.2.3
INTERCONVERSION OF N- AND O-ACYL DERIVATIVES BY ACID AND ALKALI 701
20.2.4 SELECTIVE N-BENZOYLATION 702 20.2.5 CLEAVAGE BY PER-IODATE/LEAD
TETRA-ACETATE 702 20.2.6 THE TIFFENEAU-DEMYANOV REARRANGEMENT 703 20.2.7
ARYLATION 703 CONTENTS 20.2.8 20.2.9 CHIRAL SYNTHESIS OF A-AMINO ACIDS
USE IN ASYMMETRIC REDUCTIONS AZIRIDINES 21.1 21.2 PREPARATION 21.1.1
21.1.2 21.1.3 21.1.4 21.1.5 21.1.6 21.1.7 21.1.8 21.1.9 21.1.10 21.1.11
21.1.12 21.1.13 FROM ALKENES FROM /?-AMINO ALCOHOLS THE STAUDINGER
REACTION (FROM EPOXIDES) FROM 1,1-DISUBSTITUTEDHYDRAZONES FROM
SULPHIMIDES FROM 1,2-DIOLS FROM HYDROXAMIC ACID FROM AN ENAMINE AND
PHENYL AZIDE BY DEHYDRATION OF /3-AMINO ALCOHOLS FROM A PRIMARY AMINE
AND CHLOROACETYL CHLORIDE CT-CYANOAZIRIDINES FROM A-CHLOROKETIMINES
FORMATION OF TETRACHLOROAZIRIDINES PREPARATION OF OXAZIRIDINES BY
OXIDATION OF AZIRIDINES REACTIVITY 21.2.1 21.2.2 RING-OPENING REACTIONS
WITH CHLOROFORM /3-LACTAMS (AZETIDINONES) 22.1 22.2 PREPARATION 22.1.1
22.1.2 22.1.3 22.1.4 22.1.5 22.1.6 22.1.7 22.1.8 22.1.9 22.1.10 22.1.11
22.1.12 22.1.13 22.1.14 22.1.15 FROM /?-AMINO ACIDS FROM IMINES FROM
(.SYIACTIC ALDEHYDE FROM METHYL-(/?)-3-HYDROXYBUTYRATE FROM ZINC
ENOLATES OF A-AMINO ACIDS FROM A-DIAZOKETOAMIDE FROM AN OXIME FROM AN
A-ALKYL-/?-ESTER FROM 7V-(CYANOMETHYL)AMINES FROM AZIRIDINES FROM AMIDES
FROM Y-AMINO ACIDS FROM ALLYL IODIDE FROM PHENYLSERINE USING
AF,AF-BIS(TRIMETHYLSILYL)METHOXYMETHYLAMINE FROM KETENIMINIUM SALTS
REACTIVITY 22.2.1 22.2.2 22.2.3 REDUCTION BENZOYLATION ALKYLATION 703
704 707 707 707 709 709 710 710 712 713 713 713 714 715 715 716 716 716
719 722 723 723 723 728 728 729 729 729 730 730 732 733 734 734 735 735
736 737 737 737 SUBJECT INDEX 741
|
| any_adam_object | 1 |
| author | Brown, Ben R. |
| author_facet | Brown, Ben R. |
| author_role | aut |
| author_sort | Brown, Ben R. |
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| building | Verbundindex |
| bvnumber | BV009801992 |
| callnumber-first | Q - Science |
| callnumber-label | QD305 |
| callnumber-raw | QD305.N84 |
| callnumber-search | QD305.N84 |
| callnumber-sort | QD 3305 N84 |
| callnumber-subject | QD - Chemistry |
| classification_rvk | VK 7400 |
| classification_tum | CHE 649f |
| ctrlnum | (OCoLC)28722971 (DE-599)BVBBV009801992 |
| dewey-full | 547/.44 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547/.44 |
| dewey-search | 547/.44 |
| dewey-sort | 3547 244 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Chemie |
| format | Book |
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| id | DE-604.BV009801992 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T17:41:07Z |
| institution | BVB |
| isbn | 0198557833 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-006485852 |
| oclc_num | 28722971 |
| open_access_boolean | |
| owner | DE-355 DE-BY-UBR DE-91G DE-BY-TUM DE-703 DE-11 |
| owner_facet | DE-355 DE-BY-UBR DE-91G DE-BY-TUM DE-703 DE-11 |
| physical | XXVI, 767 S. graph. Darst. |
| publishDate | 1994 |
| publishDateSearch | 1994 |
| publishDateSort | 1994 |
| publisher | Clarendon Press |
| record_format | marc |
| series | The international series of monographs on chemistry |
| series2 | The international series of monographs on chemistry |
| spelling | Brown, Ben R. Verfasser aut The organic chemistry of aliphatic nitrogen compounds B. R. Brown Oxford u.a. Clarendon Press 1994 XXVI, 767 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier The international series of monographs on chemistry 28 Azote - Composés organiques ram Composés aliphatiques ram Composés nitrés ram Stikstofverbindingen gtt Nitrogen compounds Stickstofforganische Verbindungen (DE-588)4043811-9 gnd rswk-swf Aliphatische Verbindungen (DE-588)4198956-9 gnd rswk-swf Stickstofforganische Verbindungen (DE-588)4043811-9 s Aliphatische Verbindungen (DE-588)4198956-9 s DE-604 The international series of monographs on chemistry 28 (DE-604)BV000005251 28 GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006485852&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Brown, Ben R. The organic chemistry of aliphatic nitrogen compounds The international series of monographs on chemistry Azote - Composés organiques ram Composés aliphatiques ram Composés nitrés ram Stikstofverbindingen gtt Nitrogen compounds Stickstofforganische Verbindungen (DE-588)4043811-9 gnd Aliphatische Verbindungen (DE-588)4198956-9 gnd |
| subject_GND | (DE-588)4043811-9 (DE-588)4198956-9 |
| title | The organic chemistry of aliphatic nitrogen compounds |
| title_auth | The organic chemistry of aliphatic nitrogen compounds |
| title_exact_search | The organic chemistry of aliphatic nitrogen compounds |
| title_full | The organic chemistry of aliphatic nitrogen compounds B. R. Brown |
| title_fullStr | The organic chemistry of aliphatic nitrogen compounds B. R. Brown |
| title_full_unstemmed | The organic chemistry of aliphatic nitrogen compounds B. R. Brown |
| title_short | The organic chemistry of aliphatic nitrogen compounds |
| title_sort | the organic chemistry of aliphatic nitrogen compounds |
| topic | Azote - Composés organiques ram Composés aliphatiques ram Composés nitrés ram Stikstofverbindingen gtt Nitrogen compounds Stickstofforganische Verbindungen (DE-588)4043811-9 gnd Aliphatische Verbindungen (DE-588)4198956-9 gnd |
| topic_facet | Azote - Composés organiques Composés aliphatiques Composés nitrés Stikstofverbindingen Nitrogen compounds Stickstofforganische Verbindungen Aliphatische Verbindungen |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=006485852&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV000005251 |
| work_keys_str_mv | AT brownbenr theorganicchemistryofaliphaticnitrogencompounds |