Science of Synthesis: Houben-Weyl Methods of Molecular Transformations is the entirely new edition of the acclaimed reference series Houben-Weyl, the standard synthetic chemistry resource since 1909. This new edition is published in English and will comprise 48 volumes published between the years 2000 and 2008.

Science of Synthesis is a quality reference work developed by a highly esteemed editorial board to provide a comprehensive and critical selection of reliable organic and organometallic synthetic methods. This unique resource is designed to be the first point of reference when searching for a synthesis strategy.

• Contains the expertise of presently 400 leading chemists worldwide.
• Critically evaluates the preparative applicability and significance of the synthetic methods.
• Discusses relevant background information and provides detailed experimental procedures

For full information on the Science of Synthesis series, visit the Science of Synthesis Homepage

Series Editors: D. Bellus, S. V. Ley, R. Noyori, M. Regitz, E. Schaumann, I. Shinkai, E. J. Thomas, B. M. Trost, P. J. Reider

1;Science of Synthesis - Volume 19: Three Carbon--Heteroatom Bonds: Nitriles, Isocyanides, and Derivatives;11.1;Title page;31.2;Imprint;51.3;Preface;61.4;Overview;81.5;Table of Contents;101.6;Introduction;221.7;19.1 Product Class 1: Nitrile Oxides, Sulfides, and Selenides;381.7.1;19.1.1 Product Subclass 1: Nitrile Oxides;381.7.1.1;19.1.1.1 Synthesis of Product Subclass 1;401.7.1.1.1;19.1.1.1.1 Method 1: Dehydrohalogenation of Hydroximoyl Halides;401.7.1.1.2;19.1.1.1.2 Method 2: Dehydration of Activated Nitroalkanes and Nitroalkenes;431.7.1.1.3;19.1.1.1.3 Method 3: Halogenation/Dehydrohalogenation of Aldoximes;451.7.1.1.4;19.1.1.1.4 Method 4: Dehydration of Nitroalkanes (The Mukaiyama Reaction);461.7.1.1.5;19.1.1.1.5 Method 5: Oxidation of Aldoximes;491.7.1.1.6;19.1.1.1.6 Method 6: Thermolysis of 1,2,5-Oxadiazole 2-Oxides (Furoxans);521.7.1.1.7;19.1.1.1.7 Methods 7: Miscellaneous Methods;521.7.2;19.1.2 Product Subclass 2: Nitrile Sulfides;551.7.2.1;19.1.2.1 Synthesis of Product Subclass 2;551.7.2.1.1;19.1.2.1.1 Method 1: Thermolysis of 1,3,4-Oxathiazol-2-ones;551.7.2.1.1.1;19.1.2.1.1.1 Variation 1: Thermolysis of 1,3,4-Oxathiazoles;571.7.3;19.1.3 Product Subclass 3: Nitrile Selenides;581.8;19.2 Product Class 2: Nitrile Imines;621.8.1;19.2.1 Synthesis of Product Class 2;621.8.1.1;19.2.1.1 Method 1: Dehydrohalogenation of Hydrazonoyl Halides;621.8.1.2;19.2.1.2 Method 2: Oxidation of Hydrazones;671.8.1.3;19.2.1.3 Methods 3: Miscellaneous Methods;691.8.1.3.1;19.2.1.3.1 Variation 1: From a Lithiated Diazomethane;691.8.1.3.2;19.2.1.3.2 Variation 2: Thermolysis or Photolysis of Heterocycles;701.9;19.3 Product Class 3: Nitrilium Salts;741.9.1;19.3.1 Synthesis of Product Class 3;741.9.1.1;19.3.1.1 Method 1: Dehydration of Oximes;741.9.1.2;19.3.1.2 Method 2: N-Alkylation of Nitriles;761.9.1.3;19.3.1.3 Method 3: Generation of Nitrilium Salts in Ring-Closure and Rearrangement Reactions Leading to Heterocycles;801.9.1.4;19.3.1.4 Method 4: Synthesis from Triazenyl Chlorides and Dialkylcyanamides;841.10;19.4 Product Class 4: Nitrile Ylides;881.10.1;19.4.1 Synthesis of Product Class 4;881.10.1.1;19.4.1.1 Method 1: Dehydrochlorination of Imidoyl Chlorides;881.10.1.2;19.4.1.2 Method 2: Preparation of Nitrile Ylide Equivalents;921.10.1.3;19.4.1.3 Method 3: Reaction of Nitriles with Carbenes;941.10.1.4;19.4.1.4 Method 4: Photolysis of Azirines;951.10.1.5;19.4.1.5 Methods 5: Miscellaneous Methods;971.11;19.5 Product Class 5: Nitriles;1001.11.1;19.5.1 Construction of the Cyano Group by Functional-Group Transformation from a Nitrogen-Free Starting Material;1161.11.1.1;19.5.1.1 Transformation of an Aldehyde Group;1161.11.1.1.1;19.5.1.1.1 Method 1: One-Pot Reactions Involving Intermediate Aldimines;1161.11.1.1.1.1;19.5.1.1.1.1 Variation 1: By Copper-Catalyzed Oxidation;1161.11.1.1.1.2;19.5.1.1.1.2 Variation 2: By Nickel-Catalyzed Oxidation;1171.11.1.1.1.3;19.5.1.1.1.3 Variation 3: By Oxidation with Manganese(IV) Oxide;1171.11.1.1.1.4;19.5.1.1.1.4 Variation 4: By Oxidation with Ammonium Cerium(IV) Nitrate;1181.11.1.1.1.5;19.5.1.1.1.5 Variation 5: By Oxidation with Iodine;1191.11.1.1.1.6;19.5.1.1.1.6 Variation 6: By Oxidation with Hydrogen Peroxide;1191.11.1.1.2;19.5.1.1.2 Method 2: Reactions Involving Intermediate Oximes;1201.11.1.1.2.1;19.5.1.1.2.1 Variation 1: Using Boron Trifluoride--Diethyl Ether Complex;1201.11.1.1.2.2;19.5.1.1.2.2 Variation 2: Using 4-Toluenesulfonic Acid;1211.11.1.1.2.3;19.5.1.1.2.3 Variation 3: Using Acetic Anhydride;1211.11.1.1.2.4;19.5.1.1.2.4 Variation 4: Using Phthalic Anhydride;1211.11.1.1.2.5;19.5.1.1.2.5 Variation 5: Using 1-Methylpyrrolidin-2-one;1221.11.1.1.2.6;19.5.1.1.2.6 Variation 6: Using Pyridine/Formamide;1221.11.1.1.2.7;19.5.1.1.2.7 Variation 7: Using Sodium Iodide;1231.11.1.1.2.8;19.5.1.1.2.8 Variation 8: By Dehydration with Triphosgene;1231.11.1.1.2.9;19.5.1.1.2.9 Variation 9: By Treatment with Ir