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Radical Cations

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n-C-X •+ Bond Dissociation<br />

� Iminium ion used in the “cation pool” method is generated via n-C-X •+ cleavage<br />

N<br />

CO 2Me<br />

SiMe 3<br />

N<br />

CO 2Me<br />

SiMe 3<br />

– F<br />

Bn 4NBF 4, DCM<br />

anode, –78 °C<br />

N<br />

CO 2Me<br />

� F – assisted C–Si bond cleavage<br />

–e –<br />

BF 4 –<br />

N<br />

CO 2Me<br />

J. Yoshida et al. J. Am. Chem. Soc. 2005, 127, 7324.

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