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Created by David Flaxbart
July 1997
Methoden der Organischen Chemie (Methods of Organic Chemistry, often called Houben-Weyl) is a standard reference work for chemists engaged in organic synthesis. In volumes on compound classes, including all Supplemental volumes, preparative methods are treated comprehensively and critically. Tables of examples compare the most important methods and show their scope. Detailed experimental procedures are given for the best methods. The reactivity and further reactions of each compound class are also presented. The extensive use of formula schemes help make the German-language volumes more readily understandable to non-German readers.
The 4th Edition began publication in 1952.
The base set of 16 volumes (in 70 parts) was completed in 1987,
and covers the full range of organic synthetic topics. In 1982 a Supplemental
series began (the E-volumes), which gives further and updated information
on topics covered in the base set, as well as new areas not covered earlier.
The E-series is scheduled for completion in 1999; volumes appear irregularly
and out of order. All volumes are in German until 1990, after which they
were published in English. Houben-Weyl is a textual source, and has no
online or electronic equivalent.
Houben-Weyl's German language, complex arrangement,
and lack of comprehensive indexes are obstacles to its effective use. But
organic chemists who take the time to learn its layout will find it very
useful as a tool to survey synthetic methodologies restrospectively without
consulting multiple volumes of other handbooks or Chemical Abstracts,
and often without having to locate the original journal articles.
The principal function is defined by the level of oxidation, substitution, or saturation of the carbon atom(s) to be considered. In general, higher oxidation levels have priority over lower ones and heterofunctional atoms or groups are classified by the following list of priorities:
M > Hal(F>J) > OH > OX(F > O > N) > OR > S > N > P
Index of procedures for 800 compound classes (vol.
XVI/1, pp. 1-25) and around 100,000 single compounds (pp.26-689).
| 1-4 General Chemical Methods | 16 Indexes |
| 5-15 Chemistry of Compound Classes | Supplementary Series, 1982- |
| 1 | General Laboratory Methods / 1958 |
| 1/1 | Materials / 1958 |
| 1/2 | Applied laboratory practices / 1959 |
| 2 | Analytical Methods / 1953 |
| 3 | Physical Methods / 1955 |
| 4/1A | Nonmetallic OXIDATION / 1981 |
| 4/1B | Metallic/Organic oxidation, antioxidants / 1975 |
| 4/1C-1D | REDUCTION |
| 4/2 | General chemical methods |
| 4/3 | Carbocyclic 3-member rings: / 1971 |
| ALKANES (CYCLOPROPANES) | |
| ALKENES (CYCLOPROPENES) | |
| 4/4 | Isocyclic 4-member rings: (CYCLOBUTANES) / 1971 |
| 4/4 | CYCLOPROPANES, CYCLOBUTANES (NATURAL PRODUCTS) |
| 4/5A-B | PHOTOCHEMISTRY / 1975 |
5-15 Chemistry of Compound
Classes
| 5/1A | ALKANES, CYCLOALKANES / 1970 |
| 5/1B | ALKENES (ALKENES,CYCLOALKENES,ARYLALKENES) / 1972 |
| 5/1C | ALKENES (CONJUGATED DIENES, DIELS-ALDER REACTION) / 1970 |
| 5/1D | ALKENES (POLYENES, EN-YNE) / 1972 |
| 5/2A | ACETYLENE COMPOUNDS / 1977 |
| 5/2A | ALKYNES (ACETYLENES) |
| 5/2A 913 | ALKYNES (DI AND POLY -YNES) |
| 5/2A 963 | ALLENES (ALLENES,CUMULENES) |
| 5/2A 963 | CUMULENES (ALLENES,CUMULENES) |
| 5/2B | ARENES, ARYNES / 1981 |
| 5/2B | AROMATIC COMPOUNDS |
| 5/2B | BENZYNE |
| 5/3 | FLUORINE and CHLORINE COMPOUNDS / 1962 |
| 5/4 | BROMINE and IODINE COMPOUNDS / 1960 |
| 6/1A-B | ALCOHOLS / 1979-80 |
| 6/1C | ALCOHOLS (PHENOL) / 1976 |
| 6/1C | PHENOLS |
| 6/1D | ALCOHOLS (ENOLS,EN-DIOLS) / 1978 |
| 6/1D | ALKENES (ENOLS,EN-DIOLS) |
| 6/1D | ENOLS |
| 6/1D 217 | REDUCTONES (EN-DIOLS) |
| 6/1D 303 | ALCOHOLS (BIOSYNTHESIS) |
| 6/2 | ESTERS (INORGANIC ACIDS,OXIDES,HALOGEN ACIDS) / 1963 |
| 6/2 | SILIC ACID, ORGANIC DERIVATIVES |
| 6/2 1 | METAL ALKOXIDES, PHENOLATES, ENOLATES, CHELATES |
| 6/2 171 | BORIC ACID, ORGANIC DERIVATIVES |
| 6/2 325 | NITRIC - NITROUS ACID ESTERS |
| 6/2 35 | PHENOXIDES, METAL |
| 6/2 363 | ANTIMONIC - ANTIMONIUS ACID, ORGANIC DERIVATIVES |
| 6/2 363 | ARSENIC - ARSENIOUS ACID, ORGANIC DERIVATIVES |
| 6/2 421 | SULFURIC - SULFUROUS ACID, ORGANIC DERIVATIVES |
| 6/2 487 | HYPOHALOGEN ACID ESTERS (ROX) |
| 6/2 5 | ALKOXIDES, METAL |
| 6/2 5,35,53 | ALCOHOLS (ALKOXIDES, PHENOLATES, ENOLATES |
| 6/2 503 | PERCHLORIC ACID ESTERS |
| 6/2 53 | ENOLATES, METAL |
| 6/2 561/511 | LACTONES / BETA-LACTONES |
| 6/3 1 | ETHERS / 1965 |
| 6/3 199 | ACETALS |
| 6/3 295 | ESTERS, ORTHO |
| 6/3 295 | ORTHOESTERS |
| 6/3 325 | OXONIUM SALTS |
| 6/3 367 | EPOXIDES (1,2) |
| 6/3 367,489+ | ETHERS, CYCLIC (3,4,5) |
| 6/3 689 | ACETALS, SEMICYCLIC (5) |
| 6/4 613 | ETHERS, BRIDGED / 1966 |
| 6/4 1,443+ | ETHERS, CYCLIC (6,7,8+) |
| 6/4 329,475 | ACETALS, SEMICYCLIC (6,7) |
| 6/4 505 | ETHERS, CYCLIC (1,4-0,N -0,S) |
| 6/4 587 | ACETALS, CYCLIC (1,4-0,N -0,S) |
| 6/4 677 | ACETALS, BRIDGED |
| 7/1 ; E3 | ALDEHYDES / 1975 |
| 7/2 | KETONES / 1973-77 |
| 7/2A | KETONES, SYNTHESIS |
| 7/2B | KETONES, SYNTHESIS, REACTIONS, ANALYSIS, SEPARATION |
| 7/2C | KETONES, MULTI-FUNCTIONAL |
| 7/3 | QUINONES / 1977-79 |
| 7/3A/1 | QUINONES (PARA-BENZO - PARA-NAPHTHO) |
| 7/3B | QUINONES (ORTHO-, DERIVATIVES) |
| 7/3C | QUINONES (ANTHRA-) |
| 7/4, 1 | ISATINS / 1968 |
| 7/4, 33 | QUINONES (THIONAPHTHEN-) |
| 7/4, 53 | KETENES (CARBON SUBOXIDE,THIOKETENE, ETC) |
| 8 | CARBOXYLIC ACIDS (ESTERS) / 1952 |
| 8, 1 | PEROXIDES |
| 8, 247 | NITRILES (ISONITRILES,FULMINIC ACID) |
| 8, 359 | ACIDS,CARBOXYLIC |
| 8, 503 | ESTERS, CARBOXYLIC |
| 8, 653 | AMIDES, CARBOXYLIC |
| 8, 75 | CARBONIC ACID DERIVATIVES (PHOSGENE,CYANAMIDE,ETC) |
| 8, 359 | DECARBOXYLATION |
| 9 | ORGANOSELENIUM COMPOUNDS / 1955 |
| 9 | ORGANOSULFUR COMPOUNDS |
| 9 | ORGANOTELLURIUM COMPOUNDS |
| 9 | SELENIUM COMPOUNDS |
| 9 | SULFUR COMPOUNDS |
| 9 | TELLURIUM COMPOUNDS |
| 10 | NITROGEN, ORGANONITROGEN COMPOUNDS / 1965-71 |
| 10/1 1,463 | NITRO COMPOUNDS (ALIPHATIC/AROMATIC) / 1971 |
| 10/1 1091 | HYDROXYLAMINE COMPOUNDS |
| 10/1 891,1017 | NITROSO COMPOUNDS (ALIPHATIC/AROMATIC) |
| 10/2 1 | HYDRAZINES/HYDRAZO COMPOUNDS (ALIPHATIC) |
| 10/2 123 | HYDRAZINES, ACYL (DI,TRI,TETRA) |
| 10/2 169 | HYDRAZINES/HYDRAZONES(AROMATIC) RNHNH2/RCH=N-NHR |
| 10/2 693 | HYDRAZINES/HYDRAZO COMPOUNDS (AROMATIC) |
| 10/2 71 | DIAZIRIDINES |
| 10/2 757 | AZO/AZOXY COMPOUNDS (ALIPHATIC) RN=NR/RNO=NR |
| 10/2 803 | AZOACYL COMPOUNDS |
| 10/2 823 | TRIAZINES/TETRAAZINES (ALIPHATIC) N=N-N/N-N=N-N |
| 10/2 85,823 | AZINES (C=N-N=C) TRIAZINES/TETRAZINES(ALIPHATIC) |
| 10/3 1 | DIAZONIUM SALTS (AROMATIC) / 1965 |
| 10/3 213,545 | AZO COMPOUNDS (AROMATIC) |
| 10/3 471 | AZO/AZOXY COMPOUNDS (AROMATIC-ALIPHATIC) |
| 10/3 490 | HYDRAZONES, ARYL (THROUGH COUPLING REACTIONS) |
| 10/3 627 | FORMAZANS (RN=N-CH=NNH2) |
| 10/3 695 | TRIAZINES + HIGHER HOMOLOGS (AROMATIC) |
| 10/3 745 | AZOXY COMPOUNDS (AROMATIC) |
| 10/3 777 | AZIDO COMPOUNDS (RN=N=N) |
| 10/3 837 | NITRILE OXIDES (RCNO) |
| 10/4 1 | OXIMES (=N0H) / 1968 |
| 10/4 309 | AMINE OXIDES (NITRONES) |
| 10/4 449 | OXAZIRIDINES |
| 10/4 473 | DIAZO COMPOUNDS (ALIPHATIC) |
| 10/4 895 | DIAZIRINES |
| 11/1 1 | AMINES (PREPARATION) / 1967 |
| 11/1 1034 | AMMONIA (PROPERTIES AND HANDLING) |
| 11/2 1 | AMINES (REACTIONS) 1958 |
| 11/2 223 | AZIRIDINES |
| 11/2 269 | AMINO ACIDS (+DERIVATIVES) |
| 11/2 511 | LACTAMS |
| 11/2 587 | AMMONIUM COMPOUNDS |
| 11/2 641 | AMIDES (SULFURIC, SULFUROUS, SULFAMIC ACID -) |
| 11/2 641 | SULFAMIC ACIDS (N-SUBSTITUTED) |
| 11/2 641 | SULFURIC ACID AMIDES (=N-S03H) |
| 11/2 731 | SULFUROUS ACID AMIDES (=N-S02H) |
| 12 ; E1-2 | ORGANOPHOSPHORUS COMPOUNDS / 1964 |
| 12/1 ; E1-2 | ORGANOPHOSPHORUS COMPOUNDS |
| 12/1 ; E1-2 | PHOSPHORUS COMPOUNDS (CARBON-PHOSPHORUS BONDS) |
| 12/2 | ORGANOPHOSPHORUS COMPOUNDS (ESTERS, AMIDES, ETC.) |
| 12/2 | PHOSPHORUS COMPOUNDS (ESTERS, AMIDES, ETC.) |
| 13 | ORGANOMETALLIC COMPOUNDS |
| 13/1 27 | ACID DISSOCIATION CONSTANTS (CH-ACIDS) / 1970 |
| 13/1 27 | CH-ACIDITY (PKA VALUES FOR CH ACIDS) |
| 13/1 3 | ALKALI METAL COMPOUNDS (PROPERTIES, ANALYSIS) |
| 13/1 3,255 | CESIUM COMPOUNDS |
| 13/1 3,255 | POTASSIUM COMPOUNDS |
| 13/1 3,255 | RUBIDIUM COMPOUNDS |
| 13/1 3,255 | SODIUM COMPOUNDS |
| 13/1 731 | COPPER COMPOUNDS |
| 13/1 763 | SILVER COMPOUNDS |
| 13/1 779 | GOLD COMPOUNDS |
| 13/1 87 | LITHIUM COMPOUNDS |
| 13/2A 1 | BERYLLIUM COMPOUNDS / 1973 |
| 13/2A 1,47,529 | ALKALI EARTH METAL COMPOUNDS |
| 13/2A 47 | MAGNESIUM COMPOUNDS |
| 13/2A 529 | BARIUM COMPOUNDS |
| 13/2A 529 | CALCIUM COMPOUNDS |
| 13/2A 529 | STRONTIUM COMPOUNDS |
| 13/2A 553 | ZINC COMPOUNDS |
| 13/2A 859 | CADMIUM COMPOUNDS |
| 13/2B | MERCURY COMPOUNDS / 1974 |
| 13/2B 1 | MERCURY COMPOUNDS |
| 13/3A-C | BORON COMPOUNDS / 1982-84 |
| 13/4 1 | ALUMINUM COMPOUNDS / 1970 |
| 13/4 315 | GALLIUM COMPOUNDS |
| 13/4 343 | INDIUM COMPOUNDS |
| 13/4 363 | THALLIUM COMPOUNDS |
| 13/4 391 | RARE EARTH COMPOUNDS |
| 13/5 | ORGANOSILICON COMPOUNDS / 1980 |
| 13/5 | SILICON COMPOUNDS |
| 13/6 1 | GERMANIUM COMPOUNDS / 1978 |
| 13/6 181 | TIN COMPOUNDS |
| 13/7 1 | LEAD COMPOUNDS / 1975 |
| 13/7 261 | HAFNIUM COMPOUNDS |
| 13/7 261 | TITANIUM COMPOUNDS |
| 13/7 261 | ZIRCONIUM COMPOUNDS |
| 13/7 335 | NIOBIUM COMPOUNDS |
| 13/7 335 | TANTALUM COMPOUNDS |
| 13/7 335 | VANADIUM COMPOUNDS |
| 13/7 375 | CHROMIUM COMPOUNDS |
| 13/7 429 | MOLYBDENUM COMPOUNDS |
| 13/7 485 | TUNGSTEN COMPOUNDS |
| 13/8 33 | ARSENIC COMPOUNDS / 1978 |
| 13/8 443 | ANTIMONY COMPOUNDS |
| 13/8 590 | BISMUTH COMPOUNDS |
| 13/9A | Mn, Re, Fe, Ru, Os, Pt COMPOUNDS / 1986 |
| 13/9B | Co, Rh, Ir, Ni, Pd COMPOUNDS / 1984 |
| 14 | POLYMERS/POLYMERIZATION / 1961-63 |
| 14/1 | POLYMERIZATION (VINYL/DIVINYL COMPOUNDS) |
| 14/1 | VINYL/DIVINYL COMPOUNDS (POLYMERIZATION) |
| 14/2 | POLYCONDENSATION/POLYADDITION |
| 14/2 1 | ESTERS, POLY- |
| 14/2 193 | CARBONYL/THIOCARBONYL (POLYMERIZATION) |
| 14/2 425 | CYCLIC MONOMERS |
| 14/2 48 | CARBONATES, POLY- |
| 14/2 57 | URETHANES, POLY- |
| 14/2 637,917 | POLYMER REACTIONS/ANALYSIS |
| 14/2 99 | AMIDES, POLY |
| 15/1-2 | PEPTIDES (SYNTHESIS/PURIFICATION) / 1974 |
| 16/1 p1-25 | Index of Procedures for 800 compound classes |
| 16/1 p26- | Index of Compounds to 1985 (100,000 only) |
| 16/2a | Index of 240 Acyclic compound classes; 20,000 compound subclasses (listed according to "basic principles" of HW). |
| 16/2b | Index of cyclic compounds, by ring size |
| 16/2b p.1179 | Index of name reactions and reagents |
| E1-E2 | ORGANOPHOSPHORUS COMPOUNDS / 1982 |
| E3 | ALDEHYDES / 1983 |
| E4 | CARBONIC ACID DERIVATIVES / 1983 |
| E5 | CARBOXYLIC ACID, DERIVATIVES / 1985 |
| E6 | HETARENES: 5-MEMBERED RINGS WITH ONE HETEROATOM / 1994 |
| E7 | HETARENES: 6-MEMBERED RINGS WITH ONE HETEROATOM / 1991-92 |
| E8 | HETARENES: 5-MEMBERED RINGS WITH 2+ HETEROATOMS / 1993 |
| E9 | HETARENES: 6+ MEMBERED RINGS WITH 2+ HETEROATOMS / 1998 |
| E10 | ORGANOFLUORINE COMPOUNDS / 1998 |
| E11 | ORGANOSULFUR COMPOUNDS / 1985 |
| E12B | ORGANOTELLURIUM COMPOUNDS / 1990 (IN ENGLISH) |
| E13 | ORGANOPEROXO- COMPOUNDS / 1988 |
| E14A1 | CARBONYL DERIVATIVES: O/O AND O/S ACETALS / 1991 |
| E14A2 | CARBONYL DERIVATIVES: O/N ACETALS / 1991 |
| E14A3 | CARBONYL DERIVATIVES: HAL/X-, N/S(N)- AND ANOMERIC SUGARS |
| E14B | CARBONYL DERIVATIVES: C=N DOUBLE BOND SYSTEMS / 1990 |
| E15 | EN-X, IN-X COMPOUNDS / 1993 |
| E16A | ORGANONITROGEN COMPOUNDS / 1990 |
| E16B | ORGANONITROGEN COMPOUNDS: alpha/beta LACTAMS / 1991 |
| E16C-D | ORGANONITROGEN COMPOUNDS (MISC) / 1992 |
| E17 | 3- AND 4-MEMBERED CARBOCYCLIC COMPOUNDS / 1997 |
| E18 | ORGANO-PI-METALLIC COMPOUNDS / 1986 |
| E19A | LOW-VALENCY CARBON COMPOUNDS: C-RADICALS / 1989 |
| E19B | CARBENES, CARBENOIDS / 1989 |
| E19C | CARBOCATIONS / 1990 |
| E19D | CARBOANIONS / 1993 |
| E20 | POLYMERIC MATERIALS / 1987 |
| E21 | STEREOSELECTIVE SYNTHESIS / 1996 |
| E22 | INDEXES (DUE IN 1999) |
Note: for organic compounds with elements not listed above, consult indexes in vol.16, as well as v.13, E10, E12b, E18. See also the Gmelin Handbook under the element in question.
| Mallet Chemistry Library © University of Texas at Austin |
David Flaxbart 7/97
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