Synthesis of aromatic nitriles via the temporary ...
|Title||Synthesis of aromatic nitriles via the temporary complexation of nitroarenes to the cationic cyclopentadienyliron moiety.|
|Author(s)||A. Abd-El-Aziz, W. Boraie, N. Gavel|
|Journal||Section Title: Organometallic and Organometalloidal Compounds, Organometallics|
|Abstract||Cyanide addn. to cationic cyclopentadienyliron complexes of substituted nitroarenes (I; R = 4-Me, -Et, -CHMe2, -n-Bu, -tert-Bu, -sec-Bu, -(CH)4CH3; 2-CHMe2; 2,3-, 2,4-, 3,4-, 3,5-Me2) produced nitrile adducts (II, R = same as above) where the cyano group added regioselectively in the ortho position with respect to the nitro group. Cleavage of the cyclopentadienyliron moiety via oxidative demetalation with DDQ gave functionalized benzonitriles (III, R = same as above) in good yields. Thus, I (R = 4-Me) reacted with a 7-fold excess of NaCN in DMF under mild exptl. conditions to give 72% II (R = 4-Me) which subsequently underwent oxidative demetalation with DDQ to give 83% III (R = 4-Me). [on SciFinder(R)]|
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