Selectivity, Strategy & Efficiency in Modern Organic ChemistryEdited by
- I. Fleming, University of Cambridge, UK
This volume contains 37 chapters on methods for reducing functional groups, organized into four main parts. (i) Reduction of C=X systems, where X is an electronegative heteroatom, divided into 14 chapters based on the degree of reduction, the oxidation level of the C=X substrate, and on the nature of the reagent. (ii) Reduction of X=Y systems, divided into three chapters, covering the reduction of such groups as nitro, azo, and the various kinds of P=O and S=O groups. (iii) Reduction of C=C and C≡C, divided into 12 chapters based on the method of reduction, with aromatic, heteroaromatic, and conjugated systems treated separately, and including an extensive discussion of hydrometallation. (iv) Reduction of single bonds, C-X to C-H, in eight chapters, including the hydrogenolysis of the various kinds of C-X bonds, the reduction of epoxides, and the reduction of vinyl derivatives to alkenes. Each chapter includes a discussion of chemoselectivity, regioselectivity, and stereoselectivity, wherever it is appropriate, and most include advice on the reagent of choice, and the mechanistic basis of the various methods of reduction. In short, it is, within the space available, as near to a comprehensive account of reduction in organic chemistry as one could hope for.
- Selected contents: Reduction of C=X Bonds. Reduction of C=O to CHOH by metal hydrides. Reduction of C=N to CHNH by metal hydrides. Reduction of C=X to CHXH by hydride delivery from carbon. Reduction of C=X to CHXH by dissolving metals and related methods. Reduction of C=X to CHXH by catalytic hydrogenation. Reduction of carboxylic acids to alcohols, ethers and amines. Reduction of carboxylic acids to aldehydes by metal hydrides. Reduction of carboxylic acids to aldehydes by other methods. Reduction of C=X to CH2 by dissolving metals and related methods. Reduction of X=Y Bonds. Reduction of nitro and nitroso compounds. Reduction of N=N, N-N, N-O and O-O bonds. Reduction of S=O and SO2 to S, of P=O to P, and of S-X to SH. Reduction of C=C and C≡C Bonds. Heterogeneous catalytic hydrogenation of C=C and C≡C. Homogeneous catalytic hydrogenation of C=C and C≡C. Reduction of C=C and C≡C by noncatalytic chemical methods. Partial and complete reduction of pyridines and their benzo analogs. Hydrozirconation of C=C and C≡C, and hydrometallation by other metals. Hydroboration of C=C and C≡C. Hydroalumination of C=C and C≡C. Hydrosilylation of C=C and C≡C. Reductions of C-X to C-H. Reduction of saturated alkyl halides to alkanes. Reduction of saturated alcohols and amines to alkenes. Reduction of epoxides. Reduction of ketones to alkenes. Hydrogenolysis of allyl and benzyl halides and related compounds. Reduction of &agr;-substituted carbonyl compounds-CX-CO- to carbonyl compounds -CH-CO-. Author index. Subject index.