REDUCTIVE BOND CLEAVAGE PROCESSES - II
Introduction
The carbon-heteroatom bonds in saturated alkyl alcohols, ethers, sulphides and amines cannot be cleaved by electrochemical reduction. This situation is modified substantially by the presence of an adjacent unsaturated group. Reaction can be initiated by addition of an electron to the π-antibonding orbital leading to an overall two-electron cleavage of the carbon-heteroatom bond. In the previous chapter (p. 95) rate constant data for the cleavage of benzyl sulphides and benzylpyridinium salts were used to illustrate the influence of both π-system reduction potential and nature of the leaving group on the cleavage of carbon-heteroatom bonds.
Further data from the polarography and cyclic ...
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