Reductions of CC and CC by Noncatalytic Chemical Methods

Abstract

This chapter is devoted to the discussion of the reduction of carbon-carbon double and triple bonds by noncatalytic methods. These methods include reductions by diimide, by dissolving metals in the presence or absence of proton donors, by low-valent metal ions, by metal hydride-metal halide combinations and by so-called ‘ionic hydrogenation’ procedures. Of these widely diverse methods of reduction of carbon-carbon double and triple bonds, the reduction by diimide appears to be the most versatile. The reduction of carbon-carbon double and triple bonds by diimide occurs with complete stereoselectivity and stereospecificity, and can be effected in the presence of a variety of other, very chemically reactive functional groups. The other methods of reduction of carbon-carbon double and triple bonds described in this chapter possess excellent synthetic utility in certain cases; however, their application depends critically on the structure of the unsaturated organic substrate and the reagent(s) used to effect the reduction.