Methods for Organic Electrosynthesis - Fundamentals and Applications of Organic Electrochemistry - page 79

in accord with the better overlap of the
non-bonding p orbital of oxygen with the C-Si
σ orbital than that of the orbitals of nitrogen
and sulfur [18,20,21].
Figure 4.12 Example of decrease in oxidation
potentials owing to molecular orbital
interaction
The interaction of the C-Si σ orbital is also
effective for raising the energy level of the
adjacent π systems (σ-π interaction), and the
C-Si bond is cleaved selectively. The silyl group
therefore serves as an electroauxiliary for the
oxidation of π systems. A stannyl group also
serves as an electroauxiliary for the
electrochemical oxidation of heteroatom
compounds and π systems [18].
The anodic cyanation of N -benzyl-substituted
piperizines usually provides a mixture of two