There is a vast and often bewildering array of synthetic methods and reagents available to organic chemists today. The Best Synthetic Methods series allows any scientist who is interested in the chemical transformations of molecules to choose between all the alternatives and assess their real advantages and limitations. With the emphasis on laboratory use, these volumes represent a comprehensive and practical guide to modern synthetic organic chemistry.
This book is the product of the authors many years practical experience and reading of the original literature. It contains a valuable distillation and critical evaluation of the Best Synthetic Methods for the formation and reaction of thiophenes (five membered heterocycles containing a ring sulfur) or polymers containing a thiophene functionality (thienyls). A brief review of each area is provided, but the emphasis in all cases is on describing efficient practical methods to effect the transformations described. The reader can therefore use this book to rapidly review and select the best methods of performing a synthetic conversion to create or modify a specifically substituted thiophene.
Although this book contains many references to the original literature, the large number of experimental recipes enables the user to prepare a thiophene derivative without access to the original literature. These features make the handbook especially useful for physicists working in material sciences and organic/pharmaceutical chemists, who rapidly want to find out the availability of (or how to make) a specific thiophene.
Contains a systematic description and critical evaluation of the best methods for preparation of thiophenes and polymers containing thiophenes.
Rapid location of methods achieved by systematic division of substituents following the periodic table.
All chapters are richly illustrated by detailed experimental proceedures for the synthesis of five membered heterocycles containing sulfur.
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Chapter 4C Thienylacetylenes
Chapter 4D Arylthiophenes
Chapter 4E Acylthiophenes
Chapter 4F Thiophenecarboxylic Acids and their Derivatives
Chapter 4G Thiophene Derivatives Containing Silicon Germanium Tin and Lead
Chapter 5 Syntheses of Thiophenes with Group V Substituents
Chapter 6 Syntheses of Thiophenes with Group VI Chalcogen Substituents
Chapter 7 Syntheses of Thiophenes with Group VII Substituents
Chapter 8 Bi ter and oligothienyls
2-thiophene aldehyde 3-bromothiophene acetic acid added dropwise aldehyde alkyl anhydrous anhydrous diethyl ether anhydrous tetrahydrofuran aqueous phase extracted benzene bithienyl bromide Bull butyllithium carbon Chem Chim chloroform chromatography on silica combined organic phases cooled coupling dichloromethane diethyl ether dried over magnesium dried over sodium electrophilic eluent eluent giving esters extracted with diethyl ﬁltered oﬀ ﬁltrate ﬂask followed by reaction Gronowitz halogen–metal exchange Heterocycl hexane hydrochloric acid iodide ketones lithium magnesium sulfate metalation methanol methyl mixture is reﬂuxed mixture is stirred N-bromosuccinimide N,N-dimethylformamide nitrogen obtained oxidation Perkin Trans phases are dried phases are separated phases are washed phene potassium prepared product is extracted puriﬁed by chromatography reaction mixture recrystallized residue is puriﬁed room temperature silica gel sodium bicarbonate sodium chloride solution sodium hydroxide sodium sulfate stirred at room stirring is continued sulfate and evaporated sulﬁde sulfur synthesis terthienyl Tetrahedron Lett tetrahydrofuran thiophene title compound mp Transl triethylamine washed with water yield
Page iii - ... Sturgeon: Advances in Macromolecular Carbohydrate Research Major Reference Works Barton, Nakanishi & Meth-Cohn: Comprehensive Natural Products Chemistry Katritzky, Meth-Cohn & Rees: Comprehensive Organic Functional Group Transformations Katritzky, Rees & Scriven: Comprehensive Heterocyclic Chemistry II Sainsbury: Rodd's Chemistry of Carbon Compounds Journals Bioorganic and Medicinal Chemistry Bioorganic and Medicinal Chemistry Letters Carbohydrate Research Heterocycles (distributed by Elsevier)...