Condensed thiophenes from sulfur bridging. I. Phenanthro[4,5‐bcd]thiophene

Abstract

Treatment of phenanthrene with hydrogen sulfide and an alumina catalyst at 630° gives phenthro[4,5‐bcd]thiophene (XVII). Spectral properties of XVII, its sulfoxide, and its sulfone are presented. Other examples of the direct insertion of a sulfur bridging atom into an aromatic molecule are reviewed.

Photodeoxygenation of phenanthro[4,5-bcd]thiophene S-oxide, triphenyleno[1,12-bcd]thiophene S-oxide and perylo[1,12-bcd]thiophene S-oxide

“…This synthetic procedure is similar to the previously published procedure. [4] The 1 H NMR and 13 C NMR spectra matched the structure of 6O.…”

“…[3] The 1 H NMR spectrum obtained is consistent with the previously published spectrum. [4] The and GCMS spectra matched the structure of 1.…”

Synthesis and Properties of Thieno[2′,3′,4′:4,5]naphtho[1,8-cd]pyridines

“…According to general procedure A, but using Pd(PPh 3 ) 4 (0.05 equiv) as a catalyst, 3-thienylboronic acid (1.2 equiv) and 1,4-dioxane (6 mL)/ H 2 O (1 mL) at 90 °C for 10 h provide title compound 2k as a light yellow solid in 70% yield (157. (20), 396 (27), 395 (54), 394 (68), 393 (100), 359 (51), 357 (32), 179 (32), 165 (21), 143 (22). HRMS (ESI-TOF) m/z: [M + H] + calcd for C 25 H 13 Cl 2 NS, 430.0224; found, 430.0221.…”

“…1 H NMR (300 MHz, CDCl 3 ): δ 8.73 (s, 2H), 7.86 (dd, J = 3.0 Hz, J = 1.3 Hz, 1H), 7.59 (dd, J = 5.0 Hz, J = 1.3 Hz, 1H), 7.45 (dd, J = 5.0 Hz, J = 3.0 Hz, 1H), 7.31 (s, 8H). 13 (20), 396 (27), 395 (54), 394 (68), 393 (100), 359 (51), 357 (32), 179 (32), 165 (21), 143 (22). HRMS (ESI-TOF) m/z: [M + H] + calcd for C 25 H 13 Cl 2 NS, 430.0224; found, 430.0221.…”

“…In this context, sulfur-containing heterocycles, such as tetrathiafulvalenes (TTF) or thiophenes, which represent popular π-donating building blocks in organic semiconductors, play an important role in materials science. − However, sulfur-containing pyrene derivatives have only scarcely been reported to date. Examples include peri-condensed 1,6-dithiapyrene ( A ) − and tetrathionaphthalene ( C ), naphthodithiophenes E and F , − and phenanthro­[4,5- bcd ]­thiophene ( B ) , and phenaleno­[1,9- bc ]­thiophene ( D ) , (Scheme ). Compounds A and C are isoelectronic with pyrene in its oxidation state, while B , D , E, and F represent analogs of pyrene itself.…”