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Radical Cations

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n-C-C •+ Bond Dissociation<br />

� To drive the reaction, the electrophore must be highly prone to oxidation or the resulting radical<br />

must be stabilized by a moiety on the molecule<br />

N<br />

H<br />

N<br />

H<br />

N<br />

CO 2Me<br />

V<br />

N<br />

Et<br />

H<br />

CHO 2Me<br />

Et<br />

anode,<br />

2,6-lutidine<br />

MeCN,<br />

Et 4NClO 4<br />

NaBH 4<br />

N<br />

H<br />

V<br />

N<br />

H<br />

N<br />

N<br />

CO 2Me<br />

CO2Me Et<br />

Et<br />

Et<br />

AcO<br />

MeO 2C<br />

N<br />

N<br />

H<br />

OH Me<br />

N<br />

H<br />

M. J. Gašić et al. J. Chem. Soc. Chem. Comm. 1993, 1496.<br />

N<br />

N<br />

CO 2Me<br />

–e –<br />

N<br />

Et<br />

CO 2Me<br />

OMe<br />

Et

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