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

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1;Science of Synthesis - Volume 44: Cumulenes and Allenes;1<br />1.1;Title page;3<br />1.2;Imprint;5<br />1.3;Preface;6<br />1.4;Volume Editor's Preface;8<br />1.5;Overview;10<br />1.6;Table of Contents;12<br />1.7;44 Introduction;24<br />1.7.1;44.1 Product Class 1: Cumulenes;32<br />1.7.1.1;44.1.1 Product Subclass 1: [6]- and Higher Cumulenes;33<br />1.7.1.1.1;44.1.1.1 Synthesis of Product Subclass 1;33<br />1.7.1.1.1.1;44.1.1.1.1 Synthesis by Elimination;33<br />1.7.1.1.1.1.1;44.1.1.1.1.1 Method 1: Reduction of a,.-Dihydroxypolyynes;33<br />1.7.1.1.1.1.2;44.1.1.1.1.2 Method 2: Double Elimination of Methanol from 1,7-Dimethoxyhepta-2,4-diynes;34<br />1.7.1.2;44.1.2 Product Subclass 2: Hexapentaenes ([5]Cumulenes);35<br />1.7.1.2.1;44.1.2.1 Synthesis of Product Subclass 2;35<br />1.7.1.2.1.1;44.1.2.1.1 Synthesis by Elimination;35<br />1.7.1.2.1.1.1;44.1.2.1.1.1 Method 1: Dehydroxylation of Hexa-2,4-diyne-1,6-diols;35<br />1.7.1.2.1.1.2;44.1.2.1.1.2 Method 2: Debromination of 3,4-Dibromohexa-1,2,4,5-tetraenes;36<br />1.7.1.2.1.1.3;44.1.2.1.1.3 Method 3: Other Methods Involving Elimination;371.7.1.2.1.2;44.1.2.1.2 Synthesis Mediated by Carbene Species;38<br />1.7.1.2.1.2.1;44.1.2.1.2.1 Method 1: Dimerization of Allenylidene Species;38<br />1.7.1.2.1.2.1.1;44.1.2.1.2.1.1 Variation 1: Dimerization of Allenylidene Species Generated from Propargylic Precursors;38<br />1.7.1.2.1.2.1.2;44.1.2.1.2.1.2 Variation 2: Dimerization of Allenylidene Species Generated from Bromoallenes;40<br />1.7.1.2.1.2.1.3;44.1.2.1.2.1.3 Variation 3: Dimerization of Allenylidene--Chromium Species;40<br />1.7.1.2.1.2.2;44.1.2.1.2.2 Method 2: Trapping of Hexapentaenylidene Species;40<br />1.7.1.3;44.1.3 Product Subclass 3: Pentatetraenes ([4]Cumulenes);41<br />1.7.1.3.1;44.1.3.1 Synthesis of Product Subclass 3;41<br />1.7.1.3.1.1;44.1.3.1.1 Synthesis by Substitution;41<br />1.7.1.3.1.1.1;44.1.3.1.1.1 Method 1: Lithiation and Silylation of Hexa-2,4-diynes;41<br />1.7.1.3.1.1.2;44.1.3.1.1.2 Method 2: SN2. Substitution on Penta-2,4-diynyl Esters;42<br />1.7.1.3.1.2;44.1.3.1.2 Synthesis by Elimination;43<br />1.7.1.3.1.2.1;44.1.3.1.2.1 Method 1: Double Dehydrobromination of 2,4-Dibromopenta-1,4-dienes;43<br />1.7.1.3.1.2.2;44.1.3.1.2.2 Method 2: 1,2- and 1,4-Elimination from 5-Methoxypent-2-yn-1-ols;43<br />1.7.1.3.1.2.3;44.1.3.1.2.3 Method 3: Oxidation of Hexapentaenes Followed by Carbon Monoxide Elimination;44<br />1.7.1.3.1.2.4;44.1.3.1.2.4 Method 4: Reductive 1,4-Dechlorination of a 2,5-Dichloropent-1-en-3-yne;45<br />1.7.1.3.1.2.5;44.1.3.1.2.5 Method 5: 1,1-Dehalogenation and Rearrangement of 1,1-Dihalocyclopropanes;45<br />1.7.1.3.1.2.6;44.1.3.1.2.6 Method 6: Sulfur Elimination from Penta-1,2,3,4-tetraene Episulfides;46<br />1.7.1.3.1.2.7;44.1.3.1.2.7 Method 7: Wittig Reaction;47<br />1.7.1.3.1.2.7.1;44.1.3.1.2.7.1 Variation 1: Wittig Reaction of Carbon Suboxide with Alkylidenephosphoranes;47<br />1.7.1.3.1.2.7.2;44.1.3.1.2.7.2 Variation 2: Wittig Reaction of Alka-2,3-dienoyl Chlorides with Alkylidenephosphoranes;48<br />1.7.1.3.1.2.8;44.1.3.1.2.8 Method 8: Retro-Diels--Alder Reaction;48<br />1.7.1.4;44.1.4 Product Subclass 4: Butatrienes ([3]Cumulenes);49<br />1.7.1.4.1;44.1.4.1 Synthesis of Product Subclass 4;49<br />1.7.1.4.1.1;44.1.4.1.1 Synthesis by Substitution;49<br />1.7.1.4.1.1.1;44.1.4.1.1.1 Method 1: SN2. Substitution on Pent-4-en-2-ynyl Derivatives and Related Reactions;49<br />1.7.1.4.1.1.1.1;44.1.4.1.1.1.1 Variation 1: On Pent-4-en-2-ynyl Methanesulfinates with Alkylsilver(I) Reagents;49<br />1.7.1.4.1.1.1.2;44.1.4.1.1.1.2 Variation 2: On 2-(But-3-en-1-ynyl)oxiranes with Alkylsilver(I) Reagents;50<br />1.7.1.4.1.1.1.3;44.1.4.1.1.1.3 Variation 3: Reduction of Alka-4,5-dien-2-ynols or Related Alcohols by Lithium Aluminum Hydride;50<br />1.7.1.4.1.1.2;44.1.4.1.1.2 Method 2: SN2' Substitution on 2-Bromo-1-en-3-ynes;51<br />1.7.1.4.1.1.2.1;44.1.4.1.1.2.1 Variation 1: With Alkylcopper Reagents;51<br />1.7.1.4.1.1.2.2;44.1.4.1.1.2.2 Variation 2: With Soft Carbon Nucleophiles Catalyzed by a Palladium Complex;52<br />1.7.1.4.1.1.3;44.1.4.1.1.3 Method 3: Synthesis of Phosphinobutatrienes from 2-Vinyl-1H-phosphirenes and Alkyllithium Reagents;53<br />1.7.1.4