Die vermeintlichen Aryl‐ peri ‐pyrrolino‐anthroxyle als Abkömmlinge des Benzylen‐β,β′‐benzopyrrols und über die violetten Reduktionsprodukte der α‐Cyan‐anthrachinone

Synthesis and structure of 2-phenylanthra[9,1-bc]pyrrol-6-one

“…The reduction product displayed no paramagnetic properties and was assigned the structure of 2-phenylanthra[9,1-bc]pyrrol-6-one (VII). The yield of 1.374(8)0 C 5a -C 5 1.411(12) C 10a -C 10b 1.401(11) O 1 -C 6 1.270(7)0 C 5a -C 6 1.434(12) C 10s -C 10b 1.397(10) C 2a -C 3 1.410(13) C 6a -C 7 1.380(12) C 11 -C 16 1.354(16) C 2a -C 10s 1.418(11) C 6a -C 10a 1.451(9)0 C 11 -C 12 1.389(13) C 2a -C 2 1.419(9)0 C 6a -C 6 1.474(12) C 12 -C 13 1.383(12) C 2 -C 11 1.454(10) C 7 -C 8 1.417(14) C 13 -C 14 1.384(18) C 3 -C 4 1.376(10) C 8 -C 9 1.372 (9) (7) C 10c C 2a C 2 106.6(8) O 1 C 6 C 6a 119.6(8) C 10c C 10b C 10a 121.9(6) N 1 C 2 C 2a 105.9(7) C 5a C 6 C 6a 117.6(6) C 9 C 10 C 10a 122.6(7) N 1 C 2 C 11 122.7(7) C 6a C 7 C 8 121.0(7) C 16 C 11 C 12 116.6(8) C 2a C 2 C 11 131.3(9) C 9 C 8 C 7 119.5(9) C 16 C 11 C 2 121.8(9) C 4 C 3 C 2a 120.2(9) C 10 C 9 C 8 120.5(9) C 12 C 11 C 2 121.5(9) C 3 C 4 C 5 121.9(9) C 10 C 10a C 10b 126.9(6) C 13 C 12 C 11 0120.2(12) C 10c C 5a C 5 115.4(8) C 10 C 10a C 6a 117.5(8) C 14 C 13 C 12 0121.5(12) C 10c C 5a C 6 118.1(7) C 10b C 10a C 6a 115.6(7) C 15 C 14 C 13 0118.8(10)…”

“…Sholl et al [2] showed that anthra-[9,1-bc]pyrrole derivatives can be obtained by reduction of 1-aroylanthraquinonone oximes. However, the products were assigned anthroxyl radical structure B, and later, aminyl radicals C [3]. According to [4,5], such radicals are generated by reduction of 1-cyanoanthraquinone or in the cyclization of 1-aminomethyl derivatives of 2-hydroxyanthraquinone which are obtained in turn by alkaline hydrolysis of 1-phthalimidomethyl-or trichloroacetylaminomethyl-2-hydroxyanthraquinones.…”