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internal GC standard. After stirring for 20 h at 808C aliquots were
taken from the reaction mixture and subjected to GC analysis for
determination of yield and conversion. For isolation of the products
the reaction was quenched with water. The water phase was extracted
with dichloromethane. The combined organic layers were dried over
MgSO4 and the solvents were distilled off. The product was purified
by silica gel column chromatography (70–230 mesh, n-heptane/ethyl
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3
1H NMR (400 MHz, CDCl3, 258C): d = 1.5 (d, J(H,H) = 7.2 Hz,
3H; CHCH3), 2.1 (s, 6H; 2ArCH3), 4.0 (q, 3J(H,H) = 7.2 Hz, 1H;
CH), 6.9–7.2 ppm (m, 8H; CH aromat.); 13C NMR (101 MHz, CDCl3,
258C): d = 18.3, 18.8, 20.9, 43.2, 123.8, 124.8, 126.5, 127.3, 127.9, 128.6,
133.1, 135.4, 142.8, 145.6 ppm; MS (70 eV): m/z (%): 210 (40) [M+],
195 (100) [C15H15+], 91 (10) [C7H7+].
Received: November 5, 2004
Published online: May 18, 2005
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Keywords: arylation · benzylation · Friedel–Crafts reaction ·
homogeneous catalysis · iron
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3916
ꢀ 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Angew. Chem. Int. Ed. 2005, 44, 3913 –3917