TY - JOUR
T1 - Ruthenocene 1,2-dicarboxylic acid, carboxylic anhydride, and acid chloride
T2 - A facile route to metallocene-fused acenequinones
AU - Pokharel, Uttam Raj
AU - Selegue, John P.
AU - Parkin, Sean
PY - 2011/6/27
Y1 - 2011/6/27
N2 - The dehydration of 1′,2′,3′,4′,5′- pentamethylruthenocene-1,2-dicarboxylic acid with acetic anhydride gives 1′,2′,3′,4′,5′-pentamethylruthenocene-1, 2-dicarboxylic anhydride, the first crystallographically characterized, metallocene-fused carboxylic anhydride. Treatment of the diacid with oxalyl chloride/DMF produces its 1,2-diacyl chloride, which is an excellent precursor for AlCl3-promoted double Friedel-Crafts acylation reactions with a variety of arenes, including benzene, toluene, o-xylene, p-dimethoxybenzene, and ferrocene. X-ray structural determinations of an acenequinone and a unique ferrocene/ruthenocene-fused benzoquinone show distortions attributed to strong electron donation from pentamethylruthenocene.
AB - The dehydration of 1′,2′,3′,4′,5′- pentamethylruthenocene-1,2-dicarboxylic acid with acetic anhydride gives 1′,2′,3′,4′,5′-pentamethylruthenocene-1, 2-dicarboxylic anhydride, the first crystallographically characterized, metallocene-fused carboxylic anhydride. Treatment of the diacid with oxalyl chloride/DMF produces its 1,2-diacyl chloride, which is an excellent precursor for AlCl3-promoted double Friedel-Crafts acylation reactions with a variety of arenes, including benzene, toluene, o-xylene, p-dimethoxybenzene, and ferrocene. X-ray structural determinations of an acenequinone and a unique ferrocene/ruthenocene-fused benzoquinone show distortions attributed to strong electron donation from pentamethylruthenocene.
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U2 - 10.1021/om2003915
DO - 10.1021/om2003915
M3 - Article
AN - SCOPUS:79959459935
SN - 0276-7333
VL - 30
SP - 3254
EP - 3256
JO - Organometallics
JF - Organometallics
IS - 12
ER -