New Pathways for Organic Synthesis: Practical Applications of Transition Metals

by H.M. Colquhoun, J. Holton, D.J. Thompson, M.V. Twigg

Overview

The continually growing contribution of transition metal chemistry to synthetic organic chemistry is, of course, widely recognized. Equally well­ known is the difficulty in keeping up-to-date with the multifarious reactions and procedures that seem to be spawned at an ever-increasing rate. These can certainly be summarized on the basis of reviews under the headings of the individual transition metals. More useful to the bench organic chemist, however, would be the opposite type of concordance based on the structural type of the desired synthetic product. This is the approach taken in the present monograph, which presents for each structural entity a conspectus of the transition metal-mediated processes that can be employed in its production. The resulting comparative survey should be a great help in devising the optimum synthetic approach for a particular goal. It is presented from an essentially practical viewpoint, with detailed direc­ tions interspersed in the Houben-Weyl style. The wide scope of the volume should certainly encourage synthetic organic chemists to utilize fully the range and versatility of these transition metal-mediated processes. This will certainly be a well-thumbed reference book! R. A. RAPHAEL Cambridge University v Preface In recent years an enormous amount of work has been done on the catalysis of organic reactions by various transition metal species and on the organic reactivity of organo-transition-metal compounds.

Product Details

ISBN-13:	9781461296539
Publisher:	Springer US
Publication date:	10/01/2011
Edition description:	Softcover reprint of the original 1st ed. 1984
Pages:	468
Product dimensions:	5.98(w) x 9.02(h) x 0.04(d)

Table of Contents

1. Introduction.- 2. Formation of Carbon—Carbon Bonds.- 2.1. Formation of Carbon—Carbon Single Bonds.- 2.2. Formation of Carbon—Carbon Double Bonds.- 3. Formation of Carbocyclic Compounds.- 3.1. Introduction.- 3.2. Formation of Three-Membered Rings.- 3.3. Formation of Four-Membered Rings.- 3.4. Formation of Five-Membered Rings.- 3.5. Formation of Six-Membered Rings.- 3.6. Formation of Seven-Membered Rings.- 3.7. Formation of Eight-Membered Rings.- 3.8. Formation of Large Rings (?9).- 4. Formation of Heterocyclic Compounds.- 4.1. Introduction.- 4.2. Nitrogen Heterocycles.- 4.3. Oxygen Heterocycles.- 4.4. Sulfur Heterocycles.- 4.5. Cyclic Compounds Containing Two Hetero Atoms.- 5. Isomerization of Alkenes.- 5.1. Introduction.- 5.2. Thermodynamic Considerations.- 5.3. Isolation of Organometallic Intermediates.- 5.4. Mechanisms of Catalytic Alkene Isomerization.- 5.5. Formation of a,?-Unsaturated Compounds.- 5.6. Formation of Conjugated Dienes.- 5.7. Migration into Conjugation with Aromatic Rings.- 5.8. Formation of Aromatic Compounds—Isoaromatization.- 6. Direct Introduction and Removal of Carbonyl Groups.- 6.1. Preliminaries.- 6.2. Preparation of Carboxylic Acids, Esters, and Related Derivatives.- 6.3. Preparation of Aldehydes.- 6.4. Preparation of Ketones.- 6.5. Preparation of Isocyanates.- 6.6. Decarbonylation of Aldehydes and Acyl Halides.- 7. Reduction.- 7.1. Introduction.- 7.2. Reduction of Triple Bonds.- 7.3. Reduction of Double Bonds (Nonaromatic).- 7.4. Reduction of Aromatic Systems.- 7.5. Reduction of Carbonyl Groups.- 7.6. Reduction of Nitro, Nitrile, and Other Nitrogen-Containing Functional Groups.- 7.7. Asymmetric Hydrogenation.- 7.8. Hydrogenolysis.- 8. Oxidation.- 8.1. Formation of Alcohols.- 8.2. Formation of 1,2 Diols and Amino Alcohols.- 8.3.Acetoxylation.- 8.4. Epoxidation.- 8.5. Formation of Aldehydes and Ketones.- 8.6. Formation of Acids.- 8.7. Formation of Esters.- 8.8. Dehydrogenation.- 9. Preparing and Handling Transition Metal Catalysts.- 9.1. Introduction.- 9.2. Preparation of Catalysts.- 9.3. Metal Acetylacetonates.- 9.4. Arene Metal Tricarbonyls—ArM(CO)3 (M = Cr, Mo, or W).- 9.5. Transition Metal Carbonyls.- 9.6. Recovery of Precious Metals.- 9.7. Handling Air-Sensitive Compounds.- References.- Compound Index.