Comprehensive Organic Synthesis: Reduction
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.
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Abstr acetic addition afford alcohols aldehydes aliphatic alkenes alkyl alkynes allylic aluminum hydride amides amines aromatic aryl asymmetric benzyl borane Bull carbon carbonyl carbonyl group carboxylic acids catalyst catalytic hydrogenation Chem Chemistry chemoselectivity Chim chiral chloride cleavage complex conjugated corresponding cyclic cyclohexanone deoxygenation derivatives desulfurization dienes diimide dissolving metal donor double bond enones epoxides equation equiv esters ethanol ether EtOH example formation functional groups give H. C. Brown halides Heterocycl hydrazone hydroalumination hydroboration hydrogenation hydrogenolysis hydrosilylation imine intermediate isomer isomerization ketones LiAlH4 lithium MeOH metal hydrides method methyl mixture NaBH4 nitriles nitro Organomet oxide palladium Perkin Trans presence proton Raney nickel react reaction reactive reducing agents reduction reflux regioselectivity ring salts saturated Scheme selective sodium borohydride solvent stereoselectivity steric substituted substrate sulfides Synth Synthesis synthetic temperature Tetrahedron Lett tion transition metal unsaturated vinyl yields