| |
|
|
|
|
|
|
|
|
1. |
Record Nr. |
UNINA9910830571203321 |
|
|
Autore |
Dörwald Florencio Zaragoza |
|
|
Titolo |
Side reactions in organic synthesis II : aromatic substitutions / / Florencio Zaragoza Dörwald |
|
|
|
|
|
|
|
Pubbl/distr/stampa |
|
|
Weinheim, Germany : , : Wiley-VCH Verlag GmbH & Co. KGaA, , [2014] |
|
©2014 |
|
|
|
|
|
|
|
|
|
ISBN |
|
3-527-68172-8 |
3-527-68780-7 |
3-527-68174-4 |
|
|
|
|
|
|
|
|
Edizione |
[Second edition.] |
|
|
|
|
|
Descrizione fisica |
|
1 online resource (311 p.) |
|
|
|
|
|
|
Disciplina |
|
|
|
|
|
|
Soggetti |
|
Aromatic compounds - Synthesis |
Organic compounds - Synthesis |
Aromatic compounds |
|
|
|
|
|
|
|
|
Lingua di pubblicazione |
|
|
|
|
|
|
Formato |
Materiale a stampa |
|
|
|
|
|
Livello bibliografico |
Monografia |
|
|
|
|
|
Note generali |
|
Description based upon print version of record. |
|
|
|
|
|
|
Nota di bibliografia |
|
Includes bibliographical references and index. |
|
|
|
|
|
|
Nota di contenuto |
|
Side Reactions in Organic Synthesis II; Contents; Preface; Glossary and Abbreviations; Journal Abbreviation List; Chapter 1 Electrophilic Alkylation of Arenes; 1.1 General Aspects; 1.1.1 Catalysis by Transition-Metal Complexes; 1.1.2 Typical Side Reactions; 1.2 Problematic Arenes; 1.2.1 Electron-Deficient Arenes; 1.2.2 Phenols; 1.2.3 Anilines; 1.2.4 Azoles; 1.3 Problematic Electrophiles; 1.3.1 Methylations; 1.3.2 Olefins; 1.3.3 Allylic Electrophiles; 1.3.4 Epoxides; 1.3.5 α-Haloketones and Related Electrophiles; 1.3.6 Nitroalkanes; 1.3.7 Ketones; 1.3.8 Alcohols; References |
Chapter 2 Electrophilic Olefination of Arenes2.1 General Aspects; 2.2 Olefinations with Leaving-Group-Substituted Olefins; 2.3 Olefinations with Unsubstituted Olefins; 2.4 Olefinations with Alkynes; References; Chapter 3 Electrophilic Arylation of Arenes; 3.1 General Aspects; 3.2 Arylations with Aryl Halides; 3.2.1 Via Cationic Intermediates; 3.2.2 Via Radicals; 3.2.3 Via Transition-Metal Chelates; 3.2.4 By Transition-Metal Catalysis; 3.3 Arylations with Diazonium Salts; 3.4 Arylations with Other Functionalized Arenes; 3.5 Arylations with Unsubstituted Arenes; References |
|
|
|
|
|
|
|
|
|
|
|
Chapter 4 Electrophilic Acylation of Arenes4.1 General Aspects; 4.2 Problematic Arenes; 4.2.1 Dealkylation/Isomerization of Arenes; 4.2.2 Styrenes; 4.2.3 Anilines, Phenols, and Thiophenols; 4.2.4 Electron-Deficient Arenes; 4.2.5 Azoles; 4.3 Problematic Electrophiles; 4.3.1 Problematic Acyl Halides; 4.3.2 Carboxylic Esters and Lactones; 4.3.3 Carbonic Acid Derivatives; 4.3.4 Formic Acid Derivatives; 4.3.5 Mixed Carboxylic Anhydrides and Other Polyelectrophiles; References; Chapter 5 Electrophilic Halogenation of Arenes; 5.1 General Aspects; 5.2 Typical Side Reactions; 5.3 Regioselectivity |
5.4 Catalysis5.5 Fluorinations; 5.6 Electron-Deficient Arenes; 5.6.1 Pyridines; 5.6.2 Benzoic Acid Derivatives; 5.7 Electron-Rich Arenes; 5.7.1 Phenols and Arylethers; 5.7.2 Anilines; 5.7.3 Azoles; 5.8 Sensitive Functional Groups; 5.8.1 Alkenes; 5.8.2 Amines; 5.8.3 Ethers; 5.8.4 Thiols and Thioethers; 5.8.5 Aldehydes, Ketones, and Other C-H Acidic Compounds; 5.8.6 Amides; References; Chapter 6 Electrophilic Formation of Aromatic C-N Bonds; 6.1 Nitration of Arenes; 6.1.1 Mechanisms; 6.1.2 Regioselectivity; 6.1.3 Catalysis; 6.1.4 Electron-Deficient Arenes; 6.1.5 Electron-Rich Arenes |
6.1.5.1 Anilines6.1.5.2 Indoles; 6.1.5.3 Phenols; 6.2 Electrophilic Aromatic Aminations; 6.2.1 Typical Side Reactions; 6.3 Electrophilic Aromatic Amidations; 6.3.1 Typical Side Reactions; References; Chapter 7 Electrophilic Formation of Aromatic C-S Bonds; 7.1 Sulfonylation; 7.1.1 General Aspects; 7.1.2 Typical Side Reactions; 7.2 Sulfinylation; 7.2.1 General Aspects; 7.2.2 Typical Side Reactions; 7.3 Sulfenylation; 7.3.1 General Aspects; 7.3.2 Typical Side Reactions; References; Chapter 8 Aromatic Nucleophilic Substitutions; 8.1 General Aspects; 8.1.1 Mechanisms; 8.1.2 Regioselectivity |
8.1.3 Acid-/Base-Catalysis |
|
|
|
|
|
|
Sommario/riassunto |
|
Following in the footsteps of the successful ""Side Reactions in Organic Synthesis"" by the same, highly experienced author, this new textbook focuses on aromatic substitution reactions, both electrophilic and nucleophilic.The coverage is reader-friendly with each chapter dealing with a certain reaction class in terms of its scope and limitations in detail, and unique in its approach since unexpected and unwanted side reactions are hard to find in the literature.A valuable addition to the classical textbooks on organic chemistry, this is a must-have for graduate students as well as for |
|
|
|
|
|
|
|
| |