Synthesis of aromatic nitriles via the temporary complexation of nitroarenes to the cationic cyclopentadienyliron moiety.

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
Date	1999
Volume	18
Issue	8
Start page	1562
End page	1564
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)]
DOI	10.1021/OM981022L
ISSN	0276-7333

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