W0139: Crystal Structures of Three 1-Benzenesulfonylpyrroles

W0139

Crystal Structures of Three 1-Benzenesulfonylpyrroles. David A. Grossie, Johyne P. Brooke, Scott A. Jones, Jonathan G. Grieb, P. G. Seybold and Daniel M. Ketcha, Department of Chemistry, Wright State University, Dayton, Ohio 45435 USA

The regioselectivity of Friedel-Crafts acylations of 1benzenesulfonyl pyrroles are found to be dependent on the acid promoter used. For acids that would be described as being hard, the substitution occurs at C-3, where as for soft acids it occurs at C-2. The structures of three 1-benzenesulfonylpyrroles, 1-benzenesulfonyl-4-acetylpyrrole-3-yl acetamide (I), 2-benzoyl-1-benzenesulfonylpyrrole (II), and 4-[1-(benzenesulfonyl)-2-pyrrolyl]-4-oxobutyric acid (III), have been determined as part of this investigation.

(I) Monoclinic, P2₁/c, a = 8.6730(14), b = 15.154(3), c = 11.152(3) Å, ß = 91.006(16)°, V = 1465.5(5) Å³, Z = 4, final R = 0.061 for 3223 reflections with I>3((I).

(II) Monoclinic, P2₁/c, a = 12.174(2), b = 8.283(5), c = 15.384(5) Å, ß = 106.07(2)°, V = 1490.7(10) Å³, Z = 4, final R = 0.052 for 2517 reflections with I>3((I).

(III) Monoclinic, P2₁/n, a = 11.488(3), b = 7.6580(11), c = 16.115(3) Å, ß = 96.96(2)°, V = 1407.3(5) Å₃, Z = 4, final R = 0.055 for 2752 reflections with I>3((I).